6-membered aromatics as factor Xa inhibitors

ABSTRACT

The present application describes 6-membered aromatics of formula I:or pharmaceutically acceptable salt forms thereof, wherein D may be CH2NH2 or C(=NH)NH2, which are useful as inhibitors of factor Xa.

This is a divisional of application Ser. No. 09/099,663 filed Jun. 18, 1998, now U.S. Pat. No. 6,060,491, which claims priority to Provisional Application No. 60/050,214, filed Jun. 19, 1997.

FIELD OF THE INVENTION

This invention relates generally to novel 6-membered aromatics which are inhibitors of trypsin-like serine protease enzymes, especially factor Xa, pharmaceutical compositions containing the same, and methods of using the same as anticoagulant agents for treatment and prevention of thromboembolic disorders.

BACKGROUND OF THE INVENTION

WO 96/28427 describes benzamidine anticoagulants of the formula:

wherein Z¹ and Z² are O, N(R), S or OCH₂ and the central ring may be phenyl or a variety of heterocycles. The presently claimed compounds do not contain the Z¹ linker or the substitution pattern of the above compounds.

WO 95/18111 addresses fibrinogen receptor antagonists, containing basic and acidic termini, of the formula:

wherein R¹ represents the basic termini, U is an alkylene or heteroatom linker, V may be a heterocycle, and the right hand portion of the molecule represents the acidic termini. The presently claimed compounds do not contain the acidic termini of WO 95/18111.

Activated factor Xa, whose major practical role is the generation of thrombin by the limited proteolysis of prothrombin, holds a central position that links the intrinsic and extrinsic activation mechanisms in the final common pathway of blood coagulation. The generation of thrombin, the final serine protease in the pathway to generate a fibrin clot, from its precursor is amplified by formation of prothrombinase complex (factor Xa, factor V, Ca²⁺ and phospholipid). Since it is calculated that one molecule of factor Xa can generate 138 molecules of thrombin (Elodi, S., Varadi, K.: Optimization of conditions for the catalytic effect of the factor IXa-factor VIII Complex: Probable role of the complex in the amplification of blood coagulation. Thromb. Res. 1979, 15, 617-629), inhibition of factor Xa may be more efficient than inactivation of thrombin in interrupting the blood coagulation system.

Therefore, efficacious and specific inhibitors of factor Xa are needed as potentially valuable therapeutic agents for the treatment of thromboembolic disorders. It is thus desirable to discover new factor Xa inhibitors.

SUMMARY OF THE INVENTION

Accordingly, one object of the present invention is to provide novel 6-membered aromatics which are useful as factor Xa inhibitors or pharmaceutically acceptable salts or prodrugs thereof.

It is another object of the present invention to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt or prodrug form thereof.

It is another object of the present invention to provide a method for treating thromboembolic disorders comprising administering to a host in need of such treatment a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt or prodrug form thereof.

These and other objects, which will become apparent during the following detailed description, have been achieved by the inventors'discovery that compounds of formula (I):

or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, B, D, E, M, R^(1a), R^(1b), and Z are defined below, are effective factor Xa inhibitors.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

[1] Thus, in a first embodiment, the present invention provides novel compounds of formula I:

 or a stereoisomer or pharmaceutically acceptable salt form thereof, wherein;

ring M contains from 0-4 N atoms;

D is selected from CN, C(═NR⁷)NR⁸R⁹, NHC(═NR⁷)NR⁸R⁹, NR⁸CH(═NR⁷), C(O)NR⁸R⁹, and (CR⁸R⁹)_(t)NR⁸R⁹;

E is selected from phenyl, 2-pyridyl, 4-pyridyl, pyrimidyl, and piperidinyl substituted with 1 R;

R is selected from H, F, Cl, Br, I, OR³, SR³, CO₂R³, NO₂, and CH₂OR³, and (CR⁸R⁹)_(t)NR⁸R⁹;

alternatively, E and R combine to form methylenedioxy or ethylenedioxy;

Z is selected from a bond, C₁₋₄ alkylene, (CH₂)_(r)O(CH₂)_(r), (CH₂)_(r)NR³(CH₂)_(r), (CH₂)_(r)C(O)(CH₂)_(r), (CH₂)_(r)C(O)O(CH₂)_(r), (CH₂)_(r)OC(O)(CH₂)_(r), (CH₂)_(r)C(O)NR³(CH₂)_(r), (CH₂)_(r)NR³C(O)(CH₂)_(r), (CH₂)_(r)OC(O)O(CH₂)_(r), (CH₂)_(r)OC(O)NR³(CH₂)_(r), (CH₂)_(r)NR³C(O)O(CH₂)_(r), (CH₂)_(r)NR³C(O)NR³(CH₂)_(r), (CH₂)_(r)S(O)_(p)(CH₂)_(r), (CH₂)_(r)SO₂NR³(CH₂)_(r), (CH₂)_(r)NR³SO₂(CH₂)_(r), and (CH₂)_(r)NR³SO₂NR³(CH₂)_(r), provided that Z does not form a N—-N, N—O, N—S, NCH₂N, NCH₂O, or NCH₂S bond with ring M or group A;

R^(1a) and R^(1b) are independently absent or selected from —(CH₂)_(r)—R^(1′), —CH═CH—R^(1′), NCH₂R^(1″), OCH₂R^(1″), SCH₂R^(1″), NH(CH₂)₂(CH₂)_(t)R^(1′), O(CH₂)₂(CH₂)_(t)R^(1′), and S(CH₂)₂(CH₂)_(t)R^(1′);

alternatively, R^(1a) and R^(1b), when attached to adjacent carbon atoms, together with the atoms to which they are attached form a 5-8 membered saturated, partially saturated or unsaturated ring substituted with 0-2 R⁴ and which contains from 0-2 heteroatoms selected from the group consisting of N, O, and S;

alternatively, when Z is C(O)NH and R^(1a) is attached to a ring carbon adjacent to Z, then R^(1a) is a C(O) which replaces the amide hydrogen of Z to form a cyclic imide;

R^(1′) is selected from H, C₁₋₃ alkyl, F, Cl, Br, I, —CN, —CHO, (CF₂)_(r)CF₃, (CH₂)_(r)OR², NR²R^(2a), C(O)R^(2c), OC(O)R², (CF₂)_(r)CO₂R^(2c), S(O)_(p)R^(2b), NR²(CH₂)_(r)OR², CH(═NR^(2c))NR²R^(2a), NR²C(O)R^(2b), NR²C(O)NHR^(2b), NR²C(O)₂R^(2a), OC(O)NR^(2a)R^(2b), C(O)NR²R^(2a), C(O)NR²(CH₂)_(r)OR², SO₂NR²R^(2a), NR²SO₂R^(2b), C₃₋₆ carbocyclic residue substituted with 0-2 R⁴, and 5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R⁴;

R^(1″) is selected from H, CH(CH₂OR²)₂, C(O)R^(2c), C(O)NR²R^(2a), S(O)R^(2b), S(O)₂R^(2b), and SO₂NR²R^(2a);

R², at each occurrence, is selected from H, CF₃, C₁₋₆ alkyl, benzyl, C₃₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b);

R^(2a), at each occurrence, is selected from H, CF₃, C₁₋₆ alkyl, benzyl, phenethyl, C₃₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b);

R^(2b), at each occurrence, is selected from CF₃, C₁₋₄ alkoxy, C₁₋₆ alkyl, benzyl, C₃₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b);

R^(2c), at each occurrence, is selected from CF₃, OH, C₁₋₄ alkoxy, C₁₋₆ alkyl, benzyl, C₃₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b);

alternatively, R² and R^(2a), together with the atom to which they are attached, combine to form a 5 or 6 membered saturated, partially saturated or unsaturated ring substituted with 0-2 R^(4b) and containing from 0-1 additional heteroatoms selected from the group consisting of N, O, and S;

R³, at each occurrence, is selected from H, C₁₋₄ alkyl, and phenyl;

R^(3a), at each occurrence, is selected from H, C₁₋₄ alkyl, and phenyl;

R^(3b), at each occurrence, is selected from H, C₁₋₄ alkyl, and phenyl;

R^(3c), at each occurrence, is selected from C₁₋₄ alkyl, and phenyl;

A is selected from:

C₃₋₁₀ carbocyclic residue substituted with 0-2 R⁴, and

5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R⁴;

B is selected from: H, Y, and X—Y;

X is selected from C₁₋₄ alkylene, —CR²(CR²R^(2b))(CH₂)_(t)—, —C(O)—, —C(═NR^(1″))—, —CR²(NR^(1″)R²)—, —CR²(OR²)—, —CR²(SR²)—, —C(O)CR²R^(2a)—, —CR²R^(2a)C(O), —S(O)_(p)—, —S(O)_(p)CR²R^(2a)—, —CR²R^(2a)S(O)_(p)—, —S(O)₂NR²—, —NR²S(O)₂—, —NR²S(O)₂CR²R^(2a)—, —CR²R^(2a)S(O)₂NR²—, —NR²S(O)₂NR²—, —C(O)NR²—, —NR²C(O)—, —C(O)NR²CR²R^(2a)—, —NR²C(O)CR²R^(2a)—, —CR²R^(2a)C(O)NR²—, —CR²R^(2a)NR²C(O)—, —NR²C(O)O—, —OC(O)NR²—, —NR²C(O)NR²—, —NR²—, —NR²CR²R^(2a)—, —CR²R^(2a)NR²—, O, —CR²R^(2a)O—, and —OCR²R^(2a)—;

Y is selected from:

(CH₂)_(r)NR²R^(2a), provided that X—Y do not form a N—N, O—N, or S—N bond,

C₃₋₁₀ carbocyclic residue substituted with 0-2 R^(4a), and

5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4a);

R⁴, at each occurrence, is selected from H, ═O, (CH₂)_(r)OR², F, Cl, Br, I, C₁₋₄ alkyl, —CN, NO₂, (CH₂)_(r)NR²R^(2a), (CH₂)_(r)C(O)R^(2c), NR²C(O)R^(2b), C(O)NR²R^(2a), NR²C(O)NR²R^(2a), CH(═NR²)NR²R^(2a), CH(═NS(O)₂R⁵)NR²R^(2a), NHC(═NR²)NR²R^(2a), C(O)NHC(═NR²)NR²R^(2a), SO₂NR²R^(2a), NR²SO₂NR²R^(2a), NR₂SO₂—C₁₋₄ alkyl, NR²SO₂R⁵, S(O)_(p)R⁵, (CF₂)_(r)CF₃, NCH₂R^(1″), OCH₂R^(1″), SCH₂R^(1″), N(CH₂)₂(CH₂)_(t)R^(1′), O(CH₂)₂(CH₂)_(t)R^(1′), and S(CH₂)₂(CH₂)_(t)R^(1′);

alternatively, one R⁴ is a 5-6 membered aromatic heterocycle containing from 1-4 heteroatoms selected from the group consisting of N, O, and S;

R^(4a), at each occurrence, is selected from H, ═O, (CH₂)_(r)OR², (CH₂)_(r)—F, (CH₂)_(r)—Br, (CH₂)_(r)—Cl, I, C₁₋₄ alkyl, —CN, NO₂, (CH₂)_(r)NR²R^(2a), (CH₂)_(r)NR²R^(2b), (CH₂)_(r)C(O)R^(2c), NR²C(O)R^(2b), C(O)NR²R^(2a), C(O)NH(CH₂)₂NR²R^(2a), NR²C(O)NR²R^(2a), CH(═NR²)NR²R^(2a), NHC(═NR²)NR²R^(2a), SO₂NR²R^(2a), NR²SO₂NR²R^(2a), NR²SO₂—C₁₋₄ alkyl, C(O)NHSO₂—C₁₋₄ alkyl, NR²SO₂R⁵, S(O)_(p)R⁵, and (CF₂)_(r)CF₃;

alternatively, one R^(4a) is a 5-6 membered aromatic heterocycle containing from 1-4 heteroatoms selected from the group consisting of N, O, and S and substituted with 0-1 R⁵;

R^(4b), at each occurrence, is selected from H, ═O, (CH₂)_(r)OR³, F, Cl, Br, I, C₁₋₄ alkyl, —CN, NO₂, (CH₂)_(r)NR³R^(3a), (CH₂)_(r)C(O)R³, (CH₂)_(r)C(O)OR^(3c), NR³C(O)R^(3a), C(O)NR³R^(3a), NR³C(O)NR³R^(3a), CH(═NR³)NR³R^(3a), NH³C(═NR³)NR³R^(3a), SO₂NR³R^(3a), NR³SO₂NR³R^(3a), NR³SO₂—C₁₋₄ alkyl, NR³SO₂CF₃, NR³SO₂-phenyl, S(O)_(p)CF₃, S(O)_(p)—C₁₋₄ alkyl, S(O)_(p)-phenyl, and (CF₂)_(r)CF₃;

R⁵, at each occurrence, is selected from CF₃, C₁₋₆ alkyl, phenyl substituted with 0-2 R⁶, and benzyl substituted with 0-2 R⁶;

R⁶, at each occurrence, is selected from H, OH, (CH₂)_(r)OR², F, Cl, Br, I, C₁₋₄ alkyl, CN, NO₂, (CH₂)_(r)NR²R^(2a), (CH₂)_(r)C(O)R^(2b), NR²C(O)R^(2b), NR²C(O)NR²R^(2a), CH(═NH)NH₂, NHC(═NH)NH₂, SO₂NR²R^(2a), NR²SO₂NR²R^(2a), and NR²SO₂C₁₋₄ alkyl;

R⁷, at each occurrence, is selected from H, OH, C₁₋₆ alkyl, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxy, C₁₋₄ alkoxycarbonyl, (CH₂)_(n)-phenyl, C₆₋₁₀ aryloxy, C₆₋₁₀ aryloxycarbonyl, C₆₋₁₀ arylmethylcarbonyl, C₁₋₄ alkylcarbonyloxy C₁₋₄ alkoxycarbonyl, C₆₋₁₀ arylcarbonyloxy C₁₋₄ alkoxycarbonyl, C₁₋₆ alkylaminocarbonyl, phenylaminocarbonyl, and phenyl-C₁₋₄ alkoxycarbonyl;

R⁸, at each occurrence, is selected from H, C₁₋₆ alkyl and (CH₂)_(n)-phenyl;

alternatively, R⁷ and R⁸ combine to form a 5 or 6 membered saturated, ring which contains from 0-1 additional heteroatoms selected from the group consisting of N, O, and S;

R⁹, at each occurrence, is selected from H, C₁₋₆ alkyl and (CH₂)_(n)-phenyl;

n is selected from 0, 1, 2, and 3;

m is selected from 0, 1, and 2;

p is selected from 0, 1, and 2;

r is selected from 0, 1, 2, and 3;

s is selected from 0, 1, and 2; and,

t is selected from 0 and 1.

[2] In a preferred embodiment, the present invention provides novel compounds of formulae Ia-Io:

 wherein:

Z is selected from a bond, CH₂O, OCH₂, CH₂NH, NHCH₂, CH₂C(O), C(O)CH₂, C(O)NH, C(O)NH, CH₂S(O)₂, S(O)₂(CH₂), SO₂NH, and SO₂NH;

B is selected from: Y, X—Y, and NR²R^(2a);

Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R^(4a);

phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, 1,3,4-triazole, benzofuran, benzothiofuran, indole, benzimidazole, benzoxazole, benzthiazole, indazole, benzisoxazole, benzisothiazole, and isoindazole;

Y may also be selected from the following bicyclic heteroaryl ring systems:

K is selected from O, S, NH, and N.

[3] In a more preferred embodiment, the present invention provides novel compounds of formulae:

 wherein:

D is selected from C(═NR⁷)NR⁸R⁹ and (CR⁸R⁹)_(t)NR⁸R⁹;

R is selected from H, F, Cl, OR³, CH₂R³, CH₂NH₂;

A is selected from:

piperidinyl,

piperazinyl,

C₅₋₆ carbocyclic residue substituted with 0-2 R⁴, and

5-6 membered heteroaryl containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R⁴;

Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R^(4a);

phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, and 1,3,4-triazole.

[4] In an even more preferred embodiment, the present invention provides novel compounds wherein:

E is phenyl;

D is selected from C(═NH)NH₂ and CH₂NH₂;

R is selected from H, F, Cl, and Br;

A is selected from:

C₅₋₆ carbocyclic residue substituted with 0-2 R⁴, and

5-6 membered heteroaryl containing from 1-3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R⁴;

Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R^(4a);

phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, and 1,3,4-triazole;

R², at each occurrence, is selected from H, CF₃, C₁₋₆ alkyl, benzyl, C₅₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b);

R^(2a), at each occurrence, is selected from H, CF₃, C₁₋₆ alkyl, benzyl, phenethyl, C₅₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b);

R^(2b), at each occurrence, is selected from CF₃, C₁₋₄ alkoxy, C₁₋₆ alkyl, benzyl, C₅₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b);

R^(2c), at each occurrence, is selected from CF₃, OH, C₁₋₄ alkoxy, C₁₋₆ alkyl, benzyl, C₅₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b);

alternatively, R² and R^(2a), together with the atom to which they are attached, combine to form a ring selected from imidazolyl, morpholino, piperazinyl, pyridyl, and pyrrolidinyl, substituted with 0-2 R^(4b);

R⁴, at each occurrence, is selected from H, ═O, OR², CH₂OR², F, Cl, C₁₋₄ alkyl, NR²R^(2a), CH₂NR²R^(2a), C(O)R^(2c), CH₂C(O)R^(2c), C(O)NR²R^(2a), CH(═NR²)NR²R^(2a), CH(═NS(O)₂R⁵)NR²R^(2a), SO₂NR²R^(2a), NR²SO₂—C₁₋₄ alkyl, S(O)₂R⁵, and CF₃

provided that if B is H, then R⁴ is other than tetrazole, C(O)-alkoxy, and C(O)NR²R^(2a);

R^(4a), at each occurrence, is selected from H, ═O, (CH₂)_(r)OR², F, Cl, C₁₋₄ alkyl, NR²R^(2a), CH₂NR²R^(2a), NR²R^(2b), CH₂NR²R^(2b), (CH₂)_(r)C(O)R^(2c), NR²C(O)R^(2b), C(O)NR²R^(2a), C(O)NH(CH₂)₂NR²R^(2a), NR²C(O)NR²R^(2a), SO₂NR²R^(2a), S(O)₂R⁵, and CF₃; and,

R^(4b), at each occurrence, is selected from H, ═O, (CH₂)_(r)OR³, F, Cl, C₁₋₄ alkyl, NR³R^(3a), CH₂NR³R^(3a), C(O)R³, CH₂C(O)R³, C(O)OR^(3c), C(O)NR³R^(3a), CH(═NR³)NR³R^(3a), SO₂NR³R^(3a), NR³SO₂—C₁₋₄ alkyl, NR³SO₂CF₃, NR³SO₂-phenyl, S(O)₂CF₃, S(O)₂—C₁₋₄ alkyl, S(O)₂-phenyl, and CF₃.

[5] In a further preferred embodiment, the present invention provides novel compounds selected from:

N-(2′-Aminosulfonyl-[1,1′]biphen-4-yl)-2-(3′-amidinophenyl)nicotinamide;

N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3′-amidinophenyl)nicotinamide;

N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3′-amidinophenyl)nicotinamide; and,

N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3′-carboxamidophenyl)nicotinamide;

or a pharmaceutically acceptable salt thereof.

In a second embodiment, the present invention provides novel pharmaceutical compositions, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt form thereof.

In a third embodiment, the present invention provides a novel method for treating or preventing a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt form thereof.

DEFINITIONS

The compounds herein described may have asymmetric centers. Compounds of the present invention containing an asymmetrically substituted atom may be isolated in optically active or racemic forms. It is well known in the art how to prepare optically active forms, such as by resolution of racemic forms or by synthesis from optically active starting materials. Many geometric isomers of olefins, C═N double bonds, and the like can also be present in the compounds described herein, and all such stable isomers are contemplated in the present invention. Cis and trans geometric isomers of the compounds of the present invention are described and may be isolated as a mixture of isomers or as separated isomeric forms. All chiral, diastereomeric, racemic forms and all geometric isomeric forms of a structure are intended, unless the specific stereochemistry or isomeric form is specifically indicated.

The term “substituted,” as used herein, means that any one or more hydrogens on the designated atom is replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution results in a stable compound. When a substitent is keto (i.e., ═O), then 2 hydrogens on the atom are replaced. Keto substituents are not present on aromatic moieties.

The present invention is intended to include all isotopes of atoms occurring in the present compounds. Isotopes include those atoms having the same atomic number but different mass numbers. By way of general example and without limitation, isotopes of hydrogen include tritium and deuterium. Isotopes of carbon include C-13 and C-14.

When any variable (e.g., R⁶) occurs more than one time in any constituent or formula for a compound, its definition at each occurrence is independent of its definition at every other occurrence. Thus, for example, if a group is shown to be substituted with 0-2 R⁶, then said group may optionally be substituted with up to two R⁶ groups and R⁶ at each occurrence is selected independently from the definition of R⁶. Also, combinations of substituents and/or variables are permissible only if such combinations result in stable compounds.

When a bond to a substituent is shown to cross a bond connecting two atoms in a ring, then such substituent may be bonded to any atom on the ring. When a substituent is listed without indicating the atom via which such substituent is bonded to the rest of the compound of a given formula, then such substituent may be bonded via any atom in such substituent. Combinations of substituents and/or variables are permissible only if such combinations result in stable compounds.

As used herein, “alkyl” is intended to include both branched and straight-chain saturated aliphatic hydrocarbon groups having the specified number of carbon atoms. Examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, and s-pentyl. “Haloalkyl” is intended to include both branched and straight-chain saturated aliphatic hydrocarbon groups having the specified number of carbon atoms, substituted with 1 or more halogen (for example —C_(v)F_(w) where v=1 to 3 and w=1 to (2v+1)). Examples of haloalkyl include, but are not limited to, trifluoromethyl, trichloromethyl, pentafluoroethyl, and pentachloroethyl. “Alkoxy” represents an alkyl group as defined above with the indicated number of carbon atoms attached through an oxygen bridge. Examples of alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, t-butoxy, n-pentoxy, and s-pentoxy. “Cycloalkyl” is intended to include saturated ring groups, such as cyclopropyl, cyclobutyl, or cyclopentyl. Alkenyl” is intended to include hydrocarbon chains of either a straight or branched configuration and one or more unsaturated carbon-carbon bonds which may occur in any stable point along the chain, such as ethenyl, propenyl and the like. “Alkynyl” is intended to include hydrocarbon chains of either a straight or branched configuration and one or more triple carbon-carbon bonds which may occur in any stable point along the chain, such as ethynyl, propynyl and the like.

“Halo” or “halogen” as used herein refers to fluoro, chloro, bromo, and iodo; and “counterion” is used to represent a small, negatively charged species such as chloride, bromide, hydroxide, acetate, sulfate, and the like.

As used herein, “carbocycle” or “carbocyclic residue” is intended to mean any stable 3- to 7-membered monocyclic or bicyclic or 7- to 13-membered bicyclic or tricyclic, any of which may be saturated, partially unsaturated, or aromatic. Examples of such carbocycles include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, cyclooctyl, [3.3.0]bicyclooctane, [4.3.0]bicyclononane, [4.4.0]bicyclodecane, [2.2.2]bicyclooctane, fluorenyl, phenyl, naphthyl, indanyl, adamantyl, or tetrahydronaphthyl.

As used herein, the term “heterocycle” or “heterocyclic system” is intended to mean a stable 5- to 7-membered monocyclic or bicyclic or 7- to 10-membered bicyclic heterocyclic ring which is saturated partially unsaturated or unsaturated (aromatic), and which consists of carbon atoms and from 1 to 4 heteroatoms independently selected from the group consisting of N, O and S and including any bicyclic group in which any of the above-defined heterocyclic rings is fused to a benzene ring. The nitrogen and sulfur heteroatoms may optionally be oxidized. The heterocyclic ring may be attached to its pendant group at any heteroatom or carbon atom which results in a stable structure. The heterocyclic rings described herein may be substituted on carbon or on a nitrogen atom if the resulting compound is stable. If specifically noted, a nitrogen in the heterocycle may optionally be quaternized. It is preferred that when the total number of S and O atoms in the heterocycle exceeds 1, then these heteroatoms are not adjacent to one another. It is preferred that the total number of S and O atoms in the heterocycle is not more than 1. As used herein, the term “aromatic heterocyclic system” is intended to mean a stable 5- to 7-membered monocyclic or bicyclic or 7- to 10-membered bicyclic heterocyclic aromatic ring which consists of carbon atoms and from 1 to 4 heterotams independently selected from the group consisting of N, O and S. It is preferred that the total number of S and O atoms in the aromatic heterocycle is not more than 1.

Examples of heterocycles include, but are not limited to, acridinyl, azocinyl, benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzthiazolyl, benztriazolyl, benztetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazolinyl, carbazolyl, 4aH-carbazolyl, carbolinyl, chromanyl, chromenyl, cinnolinyl, decahydroquinolinyl, 2H,6H-1,5,2-dithiazinyl, dihydrofuro[2,3-b]tetrahydrofuran, furanyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolenyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, morpholinyl, naphthyridinyl, octahydroisoquinolinyl, oxadiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolidinyl, oxazolyl, oxazolidinyl, pyrimidinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxathiinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridooxazole, pyridoimidazole, pyridothiazole, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, 6H-1,2,5-thiadiazinyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianthrenyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiophenyl, triazinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, and xanthenyl. Preferred heterocycles include, but are not limited to, pyridinyl, furanyl, thienyl, pyrrolyl, pyrazolyl, pyrrolidinyl, imidazolyl, indolyl, benzimidazolyl, 1H-indazolyl, oxazolidinyl, benzotriazolyl, benzisoxazolyl, oxindolyl, benzoxazolinyl, or isatinoyl. Also included are fused ring and spiro compounds containing, for example, the above heterocycles.

The phrase “pharmaceutically acceptable” is employed herein to refer to those compounds, materials, compositions, and/or dosage forms which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of human beings and animals without excessive toxicity, irritation, allergic response, or other problem or complication, commensurate with a reasonable benefit/risk ratio.

As used herein, “pharmaceutically acceptable salts” refer to derivatives of the disclosed compounds wherein the parent compound is modified by making acid or base salts thereof. Examples of pharmaceutically acceptable salts include, but are not limited to, mineral or organic acid salts of basic residues such as amines; alkali or organic salts of acidic residues such as carboxylic acids; and the like. The pharmaceutically acceptable salts include the conventional non-toxic salts or the quaternary ammonium salts of the parent compound formed, for example, from non-toxic inorganic or organic acids. For example, such conventional non-toxic salts include those derived from inorganic acids such as hydrochloric, hydrobromic, sulfuric, sulfamic, phosphoric, nitric and the like; and the salts prepared from organic acids such as acetic, propionic, succinic, glycolic, stearic, lactic, malic, tartaric, citric, ascorbic, pamoic, maleic, hydroxymaleic, phenylacetic, glutamic, benzoic, salicylic, sulfanilic, 2-acetoxybenzoic, fumaric, toluenesulfonic, methanesulfonic, ethane disulfonic, oxalic, isethionic, and the like.

The pharmaceutically acceptable salts of the present invention can be synthesized from the parent compound which contains a basic or acidic moiety by conventional chemical methods. Generally, such salts can be prepared by reacting the free acid or base forms of these compounds with a stoichiometric amount of the appropriate base or acid in water or in an organic solvent, or in a mixture of the two; generally, nonaqueous media like ether, ethyl acetate, ethanol, isopropanol, or acetonitrile are preferred. Lists of suitable salts are found in Remington's Pharmaceutical Sciences, 17th ed., Mack Publishing Company, Easton, Pa., 1985, p. 1418, the disclosure of which is hereby incorporated by reference.

“Prodrugs” are intended to include any covalently bonded carriers which release the active parent drug according to formula (I) in vivo when such prodrug is administered to a mammalian subject. Prodrugs of a compound of formula (I) are prepared by modifying functional groups present in the compound in such a way that the modifications are cleaved, either in routine manipulation or in vivo, to the parent compound. Prodrugs include compounds of formula (I) wherein a hydroxy, amino, or sulfhydryl group is bonded to any group that, when the prodrug or compound of formula (I) is administered to a mammalian subject, cleaves to form a free hydroxyl, free amino, or free sulfhydryl group, respectively. Examples of prodrugs include, but are not limited to, acetate, formate and benzoate derivatives of alcohol and amine functional groups in the compounds of formula (I), and the like. Preferred prodrugs are amidine prodrugs wherein D is C(═NR⁷)NH₂, and R⁷ is selected from OH, C₁₋₄ alkoxy, C₆₋₁₀ aryloxy, C₁₋₄ alkoxycarbonyl, C₆₋₁₀ aryloxycarbonyl, C₆₋₁₀ arylmethylcarbonyl, C₁₋₄ alkylcarbonyloxy C₁₋₄ alkoxycarbonyl, and C₆₋₁₀ arylcarbonyloxy C₁₋₄ alkoxycarbonyl. More preferred prodrugs are where R⁷ is OH, methoxy, ethoxy, benzyloxycarbonyl, methoxycarbonyl, and methylcarbonyloxymethoxycarbonyl.

“Stable compound” and “stable structure” are meant to indicate a compound that is sufficiently robust to survive isolation to a useful degree of purity from a reaction mixture, and formulation into an efficacious therapeutic agent.

“Substituted” is intended to indicate that one or more hydrogens on the atom indicated in the expression using “substituted” is replaced with a selection from the indicated group(s), provided that the indicated atom's normal valency is not exceeded, and that the substitution results in a stable compound. When a substituent is keto (i.e., ═O) group, then 2 hydrogens on the atom are replaced.

“Therapeutically effective amount” is intended to include an amount of a compound of the present invention or an amount of the combination of compounds claimed effective to inhibit HIV infection or treat the symptoms of HIV infection in a host. The combination of compounds is preferably a synergistic combination. Synergy, as described for example by Chou and Talalay, Adv. Enzyme Regul. 22:27-55 (1984), occurs when the effect (in this case, inhibition of HIV replication) of the compounds when administered in combination is greater than the additive effect of the compounds when administered alone as a single agent. In general, a synergistic effect is most clearly demonstrated at suboptimal concentrations of the compounds. Synergy can be in terms of lower cytotoxicity, increased antiviral effect, or some other beneficial effect of the combination compared with the individual components.

Synthesis

The compounds of the present invention can be prepared in a number of ways known to one skilled in the art of organic synthesis. The compounds of the present invention can be synthesized using the methods described below, together with synthetic methods known in the art of synthetic organic chemistry, or variations thereon as appreciated by those skilled in the art. Preferred methods include, but are not limited to, those described below. The reactions are performed in a solvent appropriate to the reagents and materials employed and suitable for the transformations being effected. It will sometimes require a judgment to modify the order of synthetic steps or to select one particular process scheme over another in order to obtain a desired compound of the invention. It will also be recognized that another major consideration in the planning of any synthetic route in this field is the judicious choice of the protecting group used for the protection of the reactive functional groups present in the compounds described in this invention. An authoritative account describing the many alternatives to the trained practitioner is Greene and Wuts (Protective Groups in Organic Chemistry, Wiley and Sons, 1991). All references cited herein are hereby incorporated in their entirety herein by reference. Compounds of this invention where B is either a carbocyclic or heterocyclic residue as defined in Formula 1 are coupled to A as shown generically and by specific example in Schemes 1 and 2, respectively. Either or both of A and B may be substituted with 0-2 R⁴. W is defined as a suitable protected nitrogen, such as NO₂ or NHBOC; a protected sulfur, such as S-tBu or SMOM; or a methyl ester. Halogen-metal exchange of the bromine in bromo-B with n-butyl lithium, quenching with triisopropyl borate and acidic hydrolysis gives the required boronic acid, B—B(OH)₂. The W—A—Br subunit may be already linked to ring M before the Suzuki coupling reaction. Deprotection provides the complete subunit.

Scheme 2 describes a typical example of how the A—B subunit is prepared for attachment to ring M. 4-Bromoaniline is protected as Boc-derivative and the coupled to 2-(t-butylamino)sulfonylphenylboronic acid under Suzuki conditions. 2-(t-Butylamino)sulfonylphenylboronic acid is prepared by the method described by Rivero (Bioorg. Med. Chem. Lett. 1994, 189). Deprotection with TFA can provide the aminobiphenyl compound. The aminobiphenyl is then coupled to the core ring structures as described below.

When B is defined as X—Y, the following description applies. Groups A and B are available either through commercial sources, known in the literature or readily synthesized by the adaptation of standard procedures known to practitioners skilled in the art of organic synthesis. the required reactive functional groups appended to analogs of A and B are also available either through commercial sources, known in the literature or readily synthesized by the adaptation of standard procedures known to practitioners skilled in the art of synthesis. In the tables that follow the chemistry required to effect the coupling of A to B is outlined.

TABLE A Preparation of Amide Ester, Urea, Sulfonamide and Sulfamide Linkages Between A and B. then the reactive to give the following If A contains: substituent of Y is: product A-X-Y: A-NHR² as a ClC(O)—Y A-NR²—C(O)—Y substituent a secondary NH ClC(O)—Y A-C(O)—Y as part of a ring or chain A-OH as a ClC(O)—Y A-O—C(O)—Y substituent A-NHR² as a ClC(O)—CR²R^(2a)—Y A-NR²—C(O)—CR²R^(2a —Y) substituent a secondary NH ClC(O)—CR²R^(2a)—Y A-C(O)—CR²R^(2a)—Y as part of a ring or chain A-OH as a ClC(O)—CR²R^(2a)—Y A-O—C(O)—CR²R^(2a)—Y substituent A-NHR²as a ClC(O)—CNR²—Y A-NR²—C(O)—CNR²—Y substituent a secondary NH ClC(O)—CNR²—Y A-C(O)—CNR²—Y as part of a ring or chain A-OH as a ClC(O)—CNR²—Y A-O—C(O)—CNR²—Y substituent A-NHR²as a ClSO²—Y A-NR²—SO₂—Y substituent a secondary NH ClSO²—Y A-SO²—Y as part of a ring or chain A-NHR²as a ClSO²—CR²R^(2a)—Y A-NR²—SO²—CR²R^(2a)—Y substituent a secondary NH ClSO²—CR²R^(2a)—Y A-SO²—CR²R^(2a)—Y as part of a ring or chain A-NHR²as a ClSO²—NR²—Y A-NR²—SO₂—NR²—Y substituent a secondary NH ClSO²—NR²—Y A-SO²—NR²—Y as part of a ring or chain A-C(O)Cl HO—Y as a A-C(O)—O—Y A-C(O)Cl NHR²—Y as a A-C(O)—NR²—Y substituent A-C(O)Cl a secondary NH as A-C(O)—Y part of a ring or chain A-CR²R^(2a)C(O)Cl HO—Y as a substituent A-CR²R^(2a)C(O)—O—Y A-CR²R^(2a)C(O)Cl NHR²—Y as a A-CR²R^(2a)C(O)—NR²—Y substituent A-CR²R^(2a)C(O)Cl a secondary NH as A-CR²R^(2a)C(O)—Y part of a ring or chain A-SO²Cl NHR²—Y as a A-SO²—NR²—Y substituent A-SO²Cl a secondary NH as A-SO_(2—Y) part of a ring or chain A-CR²R^(2a)SO₂Cl NHR²—Y as a A-CR²R^(2a)SO₂2—NR²—Y substituent A-CR²R^(2a)SO₂Cl a secondary NH as A-CR²R^(2a)SO_(2—Y) part of a ring or chain

The chemistry of Table A can be carried out in aprotic solvents such as a chlorocarbon, pyridine, benzene or toluene, at temperatures ranging from −20° C. to the reflux point of the solvent and with or without a trialkylamine base.

TABLE B Preparation of Ketone Linkages between A and B. then the reactive to give the following If A contains: substituent of Y is: product A-X-Y: A-C(O)Cl BrMg—Y A-C(O)—Y A-CR²R^(2a)C(O)Cl BrMg—Y A-CR²R^(2a)C(O)—Y A-C(O)Cl BrMgCR²R^(2a)—Y A-CR²R^(2a)C(O)—Y A-CR²R^(2a)C(O)Cl BrMgCR²R^(2a)—Y A-CR²R^(2a)C(O)CR²R^(2a)—Y

The coupling chemistry of table B can be carried out by a variety of methods. The Grignard reagent required for Y is prepared from a halogen analog of Y in dry ether, dimethoxyethane or tetrahydrofuran at 0° C. to the reflux point of the solvent. This Grignard reagent can reacted directly under very controlled conditions, that is low temperature (−20° C. or lower) and with a large excess of acid chloride or with catalytic or stoichiometric copper bromide-dimethyl sulfide complex in dimethyl sulfide as a solvent or with a variant thereof. Other methods available include transforming the Grignard reagent to the cadmium reagent and coupling according to the procedure of Carson and Prout (Org. Syn. Col. Vol. 3 (1955) 601) or a coupling mediated by Fe(acac)₃ according to Fiandanese et al. (Tetr. Lett. 1984, 4805), or a coupling mediated by manganese (II) catalysis (Cahiez and Laboue, Tetr. Lett. 1992, 33(31), 4437).

TABLE C Preparation of Ether and Thioether linkages between A and B. then the reactive to give the following If A contains: substituent of Y is: product A-X-Y: A-OH Br—Y A-O—Y A-CR²R^(2a)—OH Br—Y A-CR²R^(2a)O—Y A-OH Br—CR²R^(2a)—Y 2 A-OCR²R^(2a)—Y A-SH Br—Y A-S—Y A-CR²R^(2a)—SH Br—Y A-CR²R^(2a)S—Y A-SH Br—CR²R^(2a)—Y A-SCR²R^(2a)—Y

The ether and thioether linkages of Table C can be prepared by reacting the two components in a polar aprotic solvent such as acetone, dimethylformamide or dimethylsulfoxide in the presence of a base such as potassium carbonate, sodium hydride or potassium t-butoxide at a temperature ranging from ambient to the reflux point of the solvent used.

TABLE D Preparation of —SO—and —SO₂— linkages from thioether of Table C. then it is oxidized then it is oxidized with wet with m— If the starting Alumina/Oxone to chloroperbenzoic acid material is: give: to give: A-S—Y A-S(O)—Y A-SO₂—Y A-CR²R^(2a)S—Y A-CR²R^(2a)S(O)—Y A-CR²R^(2a)SO₂—Y A-SCR²R^(2a)—Y A-S(O)CR²R^(2a)—Y A-SO₂CR²R^(2a)—Y

The thioethers of Table C serve as a convenient starting material for the preparation of the sulfoxide and sulfone analogs of Table D. A combination of wet alumina and Oxone can provide a reliable reagents for the oxidation of the thioether to the sulfoxide as shown by Greenhalgh (Syn. Lett. 1992, 235). The sulfone can be prepared according to the method of Satoh (Chem. Lett. 1992, 381) using m-chloroperbenzoic acid.

Scheme 3 describes the synthesis of compounds wherein M is a benzene ring and Q is a protected precursor of group D of Formula I and V is a nitro, protected sulfonamide or ester group and precursor of group Z of Formula I. The V group is placed on an appropriately substituted phenol either via nitration as shown by Poirier et al. (Tetrahedron 1989, 45(5), 1415), sulfonylation as shown by Kuznetsov (Akad. Nauk SSSR Ser. Khim 1990, 8, 1888) or carboxylation by Sartori et al. (Synthesis 1988, 10, 763). Bromination with triphenylphosphine and bromine (J. Am. Chem. Soc. 1964, 86, 964) gives the desired bromide. Suzuki coupling with the appropriate boronic acid provides the desired substituted pyridine.

Schemes 4, 5, 6, and 7 describe the synthesis of compounds wherein M is pyridine and Q is a protected precursor of group D of Formula I. Each scheme represents a different substitution pattern for the pyridine ring. In Scheme 4, a suitably protected aldehyde is subjected to base-catalyzed condensation with an activated ester to give after deprotection the desired aldehyde. Refluxing with ammonium chloride as shown by Dornow and Ische (Chem. Ber. 1956, 89, 876) provides the pyridinol which is brominated with POBr₃ (Tjeenk et al. Rec. Trav. Chim. 1948, 67, 380) to give the desired 2-bromopyridine. Suzuki coupling with the appropriate boronic acid provides the desired substituted pyridine.

Treatment of an appropriately substituted 5-ethoxyoxazole with an alkene as shown by Kondrat'eva et al. Dokl. Akad. Nauk SSSR 1965, 164, 816) provides a pyridine with the V substituent at the para position. Bromination at the 3-position as shown by van der Does and Hertog (Rec. Trav. Khim. Pays-Bas 1965, 84, 951) followed by palladium-catalyzed boronic acid coupling provides the desired substituted pyridine.

Scheme 6 describes a synthesis of a third substitution pattern on a pyridine ring. The appropriate tricarbonyl compound which can be prepared by methods described in Scheme 4 is treated with ammonium chloride to form the pyridinol which is subsequently brominated. Palladium-catalyzed coupling provides the desired substituted pyridine.

Scheme 7 takes a suitably substituted dicarbonyl compound and by chemistry illustrated in Schemes 4 and 6, reacts it with ammonium chloride. Bromination gives the 3-bromopyridine which upon palladium-catalyzed coupling provides the desired substituted pyridine.

Schemes 8, 9, and 10 describe the synthesis of compounds wherein M is pyridazine and Q is a protected precursor of group D of Formula I. Each scheme represents a different substitution pattern for the pyridine ring. In Scheme 8 an activated ester is reacted with an appropriately substituted α-keto aldehyde and hydrazine as shown by Schmidt and Druey (Helv. Chim. Acta 1954, 37, 134 and 1467). Conversion of the pyridazinone to the bromide using POBr₃ and palladium-catalyzed coupling provides the desired substituted pyridazine.

In Scheme 9, glyoxal can react under basic conditions with an activated ketone and subsequently brominated/dehydro-brominated to give the desired ketoaldehyde. Alternatively, a protected ketone can react with an activated aldehyde, undergo bromination/dehydrobromination, be deprotected and oxidized to give the regioisomeric ketoaldehyde. Cyclization as shown by Sprio and Madonia (Ann. Chim. 1958, 48, 1316) with hydrazine followed by palladium-catalyzed coupling provides the desired substituted pyridazine.

By analogy to Scheme 9, in Scheme 10 a aldehyde can be reacted with an activated ketone, brominated, dehydro-brominated and deprotected to give the desired diketone. Alternatively, a regioisomeric ketone can be placed through the same reaction sequence to produce an isomeric keto aldehyde. Reaction with hydrazine followed by palladium-catalyzed coupling provides the desired substituted pyridazine.

Schemes 11, and 12 describe the synthesis of compounds wherein M is pyrimidine and Q is a protected precursor of group D of Formula I. Each scheme represents a different substitution pattern for the pyrimidine ring. In Scheme 11, a condensation with an appropriately substituted acid chloride and an activated ester followed by conjugate reduction by tin hydride (Moriya et al. J. Org. Chem. 1986, 51, 4708) gives the desired 1,4 dicarbonyl compound. Cyclization with formamidine or a substituted amidine followed by bromination gives the desired regioisomeric pyrimidine. Palladium-catalyzed coupling provides the desired substituted pyrimidine.

Using similar chemistry, Scheme 12 shows how an amidine can be condensed with a 1,3-dicarbonyl compound and subsequently brominated in the 5-position (J. Het. Chem. 1973, 10, 153) to give a specific regioisomeric bromopyrimidine. Palladium-catalyzed coupling provides the desired substituted pyrimidine.

Using the same ketoaldehyde from Scheme 12, cyclization with an appropriately substituted 1,2-diamine (Chimia 1967, 21, 510) followed by aromatization (Helv. Chim. Acta 1967, 50, 1754) provides a regioisomeric mixture of pyrazines as illustrated in Scheme 13. Bromination of the hydrobromide salt (U.S. Pat. No. 2,403,710) yields the intermediate for the palladium-catalyzed coupling step which occurs as shown above.

Schemes 14 and 15 describe the synthesis of compounds wherein M is a 1,2,3-triazine and Q is a protected precursor of group D of Formula I. In Scheme 14, a vinyl bromide is palladium coupled to a molecule containing the substituent R^(1b). Allylic bromination followed by azide displacement provide the cyclization precursor. Triphenylphosphine-mediated cyclization (J. Org. Chem. 1990, 55, 4724) give the 1-aminopyrazole which is subsequently brominated with N-bromosuccimide. Lead tetraacetate mediated rearrangement as shown by Neunhoeffer et al. (Ann. 1985, 1732) provides the desired regioisomeric 1,2,3-triazine. Palladium-catalyzed coupling provides the substituted triazine.

In Scheme 15, an alkene is allylically brominated and the bromide is displaced to give a regioisomer of the azide in Scheme 14. Following the same reaction sequence as shown above, cyclization provides the 1-aminopyrazole. Bromination followed by lead tetraacetate mediated rearrangement give the 1,2,3-triazine. Palladium-catalyzed coupling provides the other desired triazine.

Schemes 16 and 17 describe the synthesis of compounds wherein M is a 1,2,4-triazine and Q is a protected precursor of group D of Formula I. In Scheme 16, a nitrile is converted using hydrazine to give the amidrazone which is condensed with a α-ketoester to give the triazinone as shown by Paudler and Lee (J. Org. Chem. 1971, 36, 3921). Bromination as shown by Rykowski and van der Plas (J. Org. Chem. 1987, 52, 71) followed by palladium-catalyzed coupling provides the desired 1,2,4-triazine.

In Scheme 16, to achieve the opposite regioisomer the reaction scheme shown above is modify by the substituting a protect α-ketoester. This allows the most nucleophilic nitrogen to attack the ester functionality setting up the opposite regiochemistry. Deprotection and thermal cyclization gives the triazinone which is brominated as shown above. Palladium-catalyzed coupling provides the other desired 1,2,4-triazine.

Scheme 18 describes the synthesis of compounds wherein M is a 1,2,3,4-tetrazine and Q is a protected precursor of group D of Formula I. Lithiation of a vinyl bromide, transmetallation with tin, palladium catalyzed carbonylation and hydrazone formation provides a diene for a subsequent Diels-Alder reaction as shown by Carboni and Lindsey (J. Am. Chem. Soc. 1959, 81, 4342). Reaction with dibenzyl azodicarboxylate followed by catalytic hydrogenation to debenzylate and decarboxylate should give after bromination the desired 1,2,3,4-tetrazine. Palladium-catalyzed coupling provides the desired substitution.

Other features of the invention will become apparent in the course of the following descriptions of exemplary embodiments which are given for illustration fo the invention and are not intended to be limiting thereof.

EXAMPLES Example 1 N-(2′-Aminosulfonyl-[1,1′]biphen-4-yl)-2-(3′-amidinophenyl)nicotinamide, trifluoroacetic acid salt Part A. Preparation of 2-bromonicotinic acid

Potassium permanganate (18.4 g, 116 mmol) was dissolved in water (400 mL) and added to 2-bromo-3-methylpyridine (10.0 g, 58 mmol) and refluxed for 16 hours. After cooling to room temperature, the slurry was filtered through a celite plug and rinsed with water and chloroform. The entire filtrate was transferred to a separatory funnel and the layers were separated. The aqueous layer was extracted again with CHCl₃ and acidified with 6N HCl to pH 1. A white solid was obtained on standing (2.08 g of product). The pH of the remaining aqueous was adjusted to pH 4 with 2M NaOH and 2M HCl, then concentrated to <100 mL. A white precipitate was filtered. The pH was adjusted to 4 and the mixture filtered again, combining the isolated solids for a total of 3.88 g of product. The filtrate was concentrated again to <100 mL and adjusted to pH 1.5 and an additional quanitity of white solid was obtained (1.80 g), for a combined yield of 3 crops, (8.76 g, 66%). ¹H NMR (DMSO-d₆): δ13.76 (bs, 1H), 8.46 (m, 1H), 8.09 (dd, 1H, J=7.7, J′=2.2), 7.51 (m, 1H).

Part B. Preparation of methyl 2-bromonicotinate

2-Bromonicotinic acid (7.33 g, 36 mmol) was suspended in dry Et₂O (40 mL), and MeOH (2.3 mL) and diethyl azodicarboxylate (5.8 mL, 37 mmol) were added. Triphenylphosphine (9.61 g in 40 mL Et₂O, 37 mmol) was added dropwise over 2.5 hours. After stirring an additional two hours, the reaction was filtered and evaporated. The resulting clear liquid was chromatographed on silica gel (10-40% EtOAc/hexanes) to yield a clear oil (8.63 g, 100%). ¹H NMR (CDCl₁ ₃): δ8.49 (dd, 1H, J=4.8, J′=2.2), 8.09 (dd, 1H, J=7.7, J′=1.8), 7.36 (m, 1H), 3.97 (s, 3H).

Part C. Preparation of 3-cyanophenylboronic acid

3-Bromobenzonitrile (10.0 g, 55 mmol) was dissolved in dry THF (100 mL) and cooled to −100° C. (Et₂O/N₂). n-Butyllithium (24.2 mL, 2.5 M in hexane) was added over 30 minutes, maintaining the internal temp under −90°. After 20 minutes, triisopropylborate (18.0 mL) was added over 15 minutes, again maintaining the internal temperature. After the addition was complete, the reaction was allowed to warm slowly to room temperature over 1.5 hours. The reaction was stirred at room temp for 16 hours, then cooled to 15° C., after which 6 M HCl (25 mL) was added. After stirring vigorously for 3.5 hours, the reaction was partitioned between water and EtOAc. After extracting a second time with EtOAc, the combined organics were washed with 2 M NaOH. The aqueous extract was neutralized with 6 M HCl. The white precipitate was filtered, yielding the desired product (4.80 g, 60%). ¹H NMR (DMSO-d₆): δ8.37 (s, 2H), 8.10 (s, 1H), 8.03 (dt, 1H, J=7.3, J′=1.1), 7.83 (dt, 1H, J=7.6, J′=1.4), 7.53 (t, 1H, J=7.7).

Part D. Preparation of methyl 2-(3′-cyanophenyl)nicotinate

Methyl 2-bromonicotinate (2.0 g, 9.3 mmol) and 3-cyanophenylboronic acid (2.7 g, 18.4 mmol) were combined in 190 mL benzene. Sodium carbonate (19 mL of a 2 M aqueous solution), tetrabutylammonium bromide (152 mg, 0.5 mmol), and bis(triphenylphosphine)palladium(II) chloride (325 mg, 0.5 mmol) were added. The entire mixture was evacuated to remove dissolved gasses, then placed under argon. The reaction was refluxed for 14 hours, diluted with water and EtOAc, separated, dried over Na₂SO₄, filtered, and evaporated. The resulting yellow solid was chromatographed on silica gel (30% EtOAc/hexanes) to yield a light yellow solid (1.70 g, 77%). ¹H NMR (CDCl₃): δ8.81 (dd, 1H, J=4.8, J′=1.8), 8.23 (dd, 1H, J=8.0, J′=1.9), 7.85 (s, 1H), 7.73 (m, 2H), 7.55 (t, 1H, J=7.7), 7.43 (m, 1H), 3.76 (s, 3H).

Part E. Preparation of 2-(t-butylaminosulfonyl)phenylboronic acid

To a solution of 206.5 g (0.968 mol) of benzene-(N-t-butyl)sulfonamide in 2500 mL of THF under N₂ was added 790 mL (1.98 mol) of 2.5M n-butyllithium in hexane over 35 minutes, keeping the temperature between 0-5° C. The reaction mixture was allowed to warm to 10° C., at which time a thick precipitate formed. Triisopropylborate (305 mL, 1.32 mol) was added keeping the temperature below 35° C. After 1 hour, the reaction mixture was cooled, 1N HCl (1570 mL) was added, and the mixture was stirred overnight. The mixture was extracted with 400 mL of ether three times, and the combined organic extracts were extracted with 500 mL of 1N NaOH three times. The aqueous extracts were acidified to pH 1 with 6N HCl and then extracted with 500 mL ether three times. The combined ether extracts were dried over MgSO₄, and the solvents evaporated in vacuo until the volume was 700 mL. Hexane (150 mL) was added and overnight, a white precipitate formed. The solid was collected and washed with 10% ether/hexane (250 mL), then dried in vacuo to give 216.3 g (87%) of the desired compound as white crystals. m.p. 118-119° C.; ¹H NMR (CDCl₃): δ8.00 (d, 1H); 7.82 (d, 1H); 7.53 (m, 2H); 6.29 (br s, 2H); 5.13 (s, 1H); 1.18 (s, 9H).

Part F. Preparation of 4-amino-2′-t-butylaminosulfonyl-[1,1′]biphenyl

A mixture of 3.44 g (20 mmol) of 4-bromoaniline and 5.14 g (20 mmol) of 2-(t-butylaminosulfonyl)phenylboronic acid, 1.16 g of tetrakis(triphenylphosphine) palladium(0) (1 mmol), 0.32 g of tetrabutylammonium bromide (1 mmol) and 20 mL of 2M aqueous sodium carbonate were refluxed with 180 mL of benzene under N₂ for 5.5 hours. After cooling, the mixture was diluted with methylene chloride and water. The two phases were separated and the organic phase was washed with water, dried with MgSO₄ and concentrated in vacuo. The resulting thick oil was chromatographed on silica with 30% EtOAc/hexane to afford 2.52 g (41%) of the aniline. ¹H NMR (CDCl₃): δ8.14 (d, 1H); 7.53 (t, 1H); 7.43 (t, 1H); 7.33 (d, 2H); 7.27 (d, 1H); 6.76 (d, 2H); 3.7 (br s, 1H); 0.99 (s, 9H).

Part G. Preparation of N-(2′-t-butylaminosulfonyl-[1,1′]biphen-4-yl)-2-(3′-cyanophenyl)nicotinamide

Methyl 2-(3′-cyanophenyl)nicotinate (300 mg, 1.3 mmol) was combined with of 4-amino-2′-t-butylaminosulfonyl-[1,1′]biphenyl (383 mg, 1.3 mmol) in 12 mL dry CH₂Cl₂. A solution of trimethylaluminum (3.8 mL, 2.0 M in heptane) was added, and an exothermic reaction immediately occurred and the mixture darkened. The resulting solution was stirred at room temperature under argon for 3 days and then quenched carefully with a few drops of 1 M HCl. An emulsion was obtained on dilution with EtOAc and water. The layers were separated, and the organic was extracted again with water and brine, dried over Na₂SO₄, filtered, and evaporated. A small amount of additional material was obtained from the aqueous extract by adjusting the pH to 8 with sat. NaHCO₃ and extracting with EtOAc. This material was dried over Na₂SO₄, filtered, evaporated, and combined with the previous extract for chromatography on silica gel (50-60% EtOAc/hexanes) to yield the desired product (190 mg, 30%). ¹H NMR (CDCl₃): δ8.86 (dd, 1H, J=4.7, J′=1.9), 8.14 (m, 3H), 8.00 (d, 1H, J=7.7), 7.73 (d, 1H, J=8.1), 7.50 (m, 9H), 7.29 (dd, 1H, J=7.4, J′=1.1), 3.60 (s, 1H), 1.02 (s, 9H).

Part H. Preparation of N-(2′-aminosulfonyl-[1,1′]biphen-4-yl)-2-(3′-amidinophenyl)nicotinamide, trifluoroacetic acid salt

N-(2′-t-butylaminosulfonyl-[1,1′]biphen-4-yl)-2-(3′-cyanophenyl)nicotinamide (190 mg, 0.37 mmol) was dissolved in dry MeOH (10 mL) and cooled to 0° C. HCl(g) was generated by the addition of concentrated H₂SO₄ (60 mL) to NaCl (240 g) over 40 minutes and was bubbled into the reaction mixture. The gas was permitted to continue bubbling through the reaction for 3 hours after the H₂SO₄ addition was complete. At this point, the HCl generator and ice bath were removed, and the reaction stirred under argon for 19 hours. This solution was then evaporated, placed under high vacuum, and redissolved in dry MeOH (10 mL). Ammonium carbonate (200 mg) was added, stirred for 24 hours under argon, and evaporated. The product was purified by preparative HPLC on a C-18 reverse phase column (10-70% MeCN/H₂O/0.05% TFA), yielding a white powder (140 mg, 54%). ¹H NMR (DMSO-d₆): δ10.65 (s, 1H), 9.38 (s, 2H), 8.92 (s, 2H), 8.81 (dd, 1H, J=4.4, J′=1.4), 8.10 (m, 2H), 7.97 (m, 2H), 7.76 (m, 1H), 7.67 (t, 1H, J=8.0), 7.57 (m, 5H), 7.29 (m, 5H). HRMS calc. for C₂₅H₂₂N₅O₃S: m/z 472.1443; found, 472.1457.

Examples 2, 3 and 4 N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3′-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 2), N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3′-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 3), and N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3′-carboxamidophenyl)nicotinamide, trifluoroacetic acid salt (Example 4) Part A. Preparation of 2-(3′-cyanophenyl)nicotinic acid

Methyl 2-(3′-cyanophenyl)nicotinate (1.21 g, 5.1 mmol) was partially dissolved in MeOH (40 mL), and lithium hydroxide monohydrate (234 mg dissolved in 6 mL H₂O, 5.6 mmol) was added. After 20 hours, the resulting solution was diluted with water and extracted with CHCl₃. The aqueous was acidified to pH 4 with 1 M HCl and extracted several times with CHCl₃. Solid sodium chloride was added to the aqueous solution and the solution was extracted with 5-10% MeOH/CHCl₃. The organic extracts were combined, dried over Na₂SO₄, filtered, and evaporated to yield a white solid (1.06 g, 93%). ¹H NMR (CDCl₃): δ8.85 (dd, 1H, J=5.1, J′=1.5), 8.35 (dd, 1H, J=7.6, J′=1.4), 7.84 (s, 1H), 7.75 (m, 2H), 7.55 (t, 1H, J=7.7), 7.47 (m, 1H).

Part B. Preparation of 2-amino-5-(2-t-butylamino-sulfonyl)phenylpyridine

A mixture of 1.55 g (9.0 mmol) of 2-amino-5-bromopyridine and 2.3 g (9.0 mmol) of 2-(t-butylaminosulfonyl)phenylboronic acid, 0.52 g of tetrakis(triphenylphosphine) palladium(0) (0.45 mmol), 0.15 g of tetrabutylammonium bromide (0.45 mmol) and 9 mL of 2M aqueous sodium carbonate were refluxed with 80 mL of benzene under Ar for 5 hours. After cooling, the mixture was diluted with 25 mL of methylene chloride and 25 mL of water. The two phases were separated and the organic phase was washed with water, dried with MgSO₄ and concentrated in vacuo. The resulting thick oil was chromatographed on silica with 50% EtOAc/hexane to afford 1.34 g (49%) of the aniline. ¹H NMR (CDCl₃): δ8.18 (d, 1H); 8.07 (m, 1H); 7.70 (dd, 1H); 7.58 (dt, 1H); 7.48 (dt, 1H); 7.28 (d, 1H); 6.56 (d, 1H); 4.62 (br s, 2H); 3.88 (br s, 1H); 1.06 (s, 9H).

Part C. Preparation of N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3′-cyanophenyl)nicotinamide

2-(3′-cyanophenyl)nicotinic acid (300 mg, 1.3 mmol) was suspended in 5 mL dry CH₂Cl₁ ₂, and oxalyl chloride (175 μl, 2.0 mmol) was added, followed by 2 drops of dry DMF. The reaction stirred at room temperature under argon for 2 hours and then evaporated. This solid was redissolved in 8 mL dry CH₂Cl₂, and dimethylaminopyridine (490 mg, 4.0 mmol) was added, followed by 2-amino-5-(2-t-butylaminosulfonyl)phenylpyridine (410 mg, 1.3 mmol). The reaction was stirred 3 days at room temperature, diluted with CH₂Cl₂, extracted with saturated NaHCO₃, dried over Na₂SO₄, filtered, and evaporated. The resulting material was chromatographed on silica gel (50-75% EtOAc/hexanes) to yield the desired product (423 mg, 62%). ¹H NMR (CDCl₃): δ8.83 (dd, 1H, J=4.8, J′=1.5), 8.40 (bs, 1H), 8.29 (bd, 1H, J=8.4), 8.17 (dd, 1H), J=8.0, J′=1.1), 8.09 (m, 3H), 7.97 (d, 1H, J=7.7), 7.79 (d, 1H, J=8.4), 7.69 (d, 1H, J=7.7), 7.54 (m, 4H), 7.25 (m, 1H), 4.19 (bs, 1H), 1.08 (s, 9H).

Part D. Preparation of N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3′-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 2), N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3′-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 3), and N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3′-carboxamidophenyl)nicotinamide, trifluoroacetic acid salt (Example 4)

N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3′-cyanophenyl)nicotinamide (410 mg, 1.03) was dissolved in a mixture of dry MeOH (5 mL) and dry CHCl₃ (15 mL) and cooled to 0° C. HCl(g) was generated by the addition of concentrated H₂SO₄ (45 mL) to NaCl (220 g) over 55 min and was bubbled into the reaction mixture. The HCl generator and ice bath were removed, and the reaction was stirred under argon for 16 hours and evaporated. The resulting solid was redissolved in dry MeOH (15 mL), and ammonium carbonate (385 mg) was added. The reaction was stirred 19 hours at room temperature under argon and evaporated. The resulting solid was purified by preparative HPLC on a C-18 reverse phase column (5-70% MeCNH/H2O/0.05% TFA) to yield N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3′-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 2), (250 mg, 45%). ¹H NMR (DMSO-d₆): δ11.27 (s, 1H), 9.43 (s, 2H), 8.98 (s, 2H), 8.83 (dd, 1H, J=4.8, J′=1.9), 8.32 (s, 1H), 8.13 (m, 2H), 8.05 (m, 2H), 7.96 (d, 1H, J=7.3), 7.81 (d, 2H, J=8.4), 7.65 (m, 4H), 7.47 (s, 2H), 7.37 (m, 1H). HRMS calc. for C₂₄H₂₁N₆O₃S: m/z 473.1396; found, 473.1397. A second product, N-[5-(2-t-butylaminosulfonyl)-phenylpyrid-2-yl]-2-(3′-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 3), was also obtained (58 mg, 10%). ¹H NMR (DMSO-d₆): δ9.7 (s, 1H), 9.41 (s, 2H), 8.95 (s, 2H), 8.82 (m, 1H), 8.28 (s, 1H), 8.09 (m, 4H), 7.95 (d, 1H, J=7.7), 7.79 (m, 2H), 7.63 (m, 4H), 7.34 (d, 1H, J=7.7), 7.18 (s, 1H), 1.04 (s, 9H). HRMS calc. for C₂₈H₂₉N₆O₃S: 529.2022; found, 529.2050. A third product, N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3′-carboxamidophenyl)nicotinamide, trifluoroacetic acid salt (Example 4) was isolated and chromatographed on silica gel (10-20% MeOH/CHCl₃) to yield a white solid (77 mg, 20%). ¹H NMR (DMSO-d₆): δ11.13 (s, 1H), 8.75 (dd, 1H, J=4.8, J′=1.9), 8.26 (m, 2H), 8.02 (m, 4H), 7.84 (d, 1H, J=7.7), 7.74 (m, 2H), 7.59 (m, 2H), 7.47 (m, 2H), 7.36 (m, 4H).

TABLE 1

MS Ex D R₂ A′ (M + H)⁺ 1 C(═NH)NH₂ SO₂NH₂ CH 472.1 2 C(═NH)NH₂ SO₂NH₂ N 473.1 3 C(═NH)NH₂ SO₂NHtBu N 529.2 4 C(O)NH₂ SO₂NH₂ N 474.1

The following table contains representative examples of the present invention. Each entry in the table is intended to be paired with each formulae at the start of the table. For example, example 1 in Table 2 is intended to be paired with each of formulae a₁-ss₄.

TABLE 2

a₁ R = F, D = NH₂ b₁ R = F, D = NH₂ c₁ R = F, D = NH₂ a₂ R = H, D = NH₂ b₂ R = H, D = NH₂ c₂ R = H, D = NH₂ a₃ R = F, D = CH₂NH₂ b₃ R = F, D = CH₂NH₂ c₃ R = F, D = CH₂NH₂ a₄ R = H, D = CH₂NH₂ b₄ R = H, D = CH₂NH₂ c₄ R = H, D = CH₂NH₂ a₅ R = F, D = C(═NH)NH₂ b₅ R = F, D = C(═NH)NH₂ c₅ R = F, D = C(═NH)NH₂ a₆ R = H, D = C(═NH)NH₂ b₆ R = H, D = C(═NH)NH₂ c₆ R = H, D = C(═NH)NH₂ a₇ R = F, D = C(O)NH₂ b₇ R = F, D = C(O)NH₂ c₇ R = F, D = C(O)NH₂ a₈ R = H, D = C(O)NH₂ b₈ R = H, D = C(O)NH₂ c₈ R = H, D = C(O)NH₂

d₁ R = F, D = NH₂ e₁ R = F, D = NH₂ f₁ R = F, D = NH₂ d₂ R = H, D = NH₂ e₂ R = H, D = NH₂ f₂ R = H, D = NH₂ d₃ R = F, D = CH₂NH₂ e₃ R = F, D = CH₂NH₂ f₃ R = F, D = CH₂NH₂ d₄ R = H, D = CH₂NH₂ e₄ R = H, D = CH₂NH₂ f₄ R = H, D = CH₂NH₂ d₅ R = F, D = C(═NH)NH₂ e₅ R = F, D = C(═NH)NH₂ f₅ R = F, D = C(═NH)NH₂ d₆ R = H, D = C(═NH)NH₂ e₆ R = H, D = C(═NH)NH₂ f₆ R = H, D = C(═NH)NH₂ d₇ R = F, D = C(O)NH₂ e₇ R = F, D = C(O)NH₂ f₇ R = F, D = C(O)NH₂ d₈ R = H, D = C(O)NH₂ e₈ R = H, D = C(O)NH₂ f₈ R = H, D = C(O)NH₂

g₁ R = F, D = NH₂ h₁ R = F, D = NH₂ i₁ R = F, D = NH₂ g₂ R = H, D = NH₂ h₂ R = H, D = NH₂ i₂ R = H, D = NH₂ g₃ R = F, D = CH₂NH₂ h₃ R = F, D = CH₂NH₂ i₃ R = F, D = CH₂NH₂ g₄ R = H, D = CH₂NH₂ h₄ R = H, D = CH₂NH₂ i₄ R = H, D = CH₂NH₂ g₅ R = F, D = C(═NH)NH₂ h₅ R = F, D = C(═NH)NH₂ i₅ R = F, D = C(═NH)NH₂ g₆ R = H, D = C(═NH)NH₂ h₆ R = H, D = C(═NH)NH₂ i₆ R = H, D = C(═NH)NH₂ g₇ R = F, D = C(O)NH₂ h₇ R = F, D = C(O)NH₂ i₇ R = F, D = C(O)NH₂ g₈ R = H, D = C(O)NH₂ h₈ R = H, D = C(O)NH₂ i₈ R = H, D = C(O)NH₂

j₁ R = F, D = NH₂ k₁ R = F, D = NH₂ l₁ R = F, D = NH₂ j₂ R = H, D = NH₂ k₂ R = H, D = NH₂ l₂ R = H, D = NH₂ j₃ R = F, D = CH₂NH₂ k₃ R = F, D = CH₂NH₂ l₃ R = F, D = CH₂NH₂ j₄ R = H, D = CH₂NH₂ k₄ R = H, D = CH₂NH₂ l₄ R = H, D = CH₂NH₂ j₅ R = F, D = C(═NH)NH₂ k₅ R = F, D = C(═NH)NH₂ l₅ R = F, D = C(═NH)NH₂ j₆ R = H, D = C(═NH)NH₂ k₆ R = H, D = C(═NH)NH₂ l₆ R = H, D = C(═NH)NH₂ j₇ R = F, D = C(O)NH₂ k₇ R = F, D = C(O)NH₂ l₇ R = F, D = C(O)NH₂ j₈ R = H, D = C(O)NH₂ k₈ R = H, D = C(O)NH₂ l₈ R = H, D = C(O)NH₂

m₁ R = F, D = NH₂ n₁ R = F, D = NH₂ o₁ R = F, D = NH₂ m₂ R = H, D = NH₂ n₂ R = H, D = NH₂ o₂ R = H, D = NH₂ m₃ R = F, D = CH₂NH₂ n₃ R = F, D = CH₂NH₂ o₃ R = F, D = CH₂NH₂ m₄ R = H, D = CH₂NH₂ n₄ R = H, D = CH₂NH₂ o₄ R = H, D = CH₂NH₂ m₅ R = F, D = C(═NH)NH₂ n₅ R = F, D = C(═NH)NH₂ o₅ R = F, D = C(═NH)NH₂ m₆ R = H, D = C(═NH)NH₂ n₆ R = H, D = C(═NH)NH₂ o₆ R = H, D = C(═NH)NH₂ m₇ R = F, D = C(O)NH₂ n₇ R = F, D = C(O)NH₂ o₇ R = F, D = C(O)NH₂ m₈ R = H, D = C(O)NH₂ n₈ R = H, D = C(O)NH₂ o₈ R = H, D = C(O)NH₂

p₁ R = F, D = NH₂ q₁ R = F, D = NH₂ r₁ R = F, D = NH₂ p₂ R = Cl, D = NH₂ q₂ R = Cl, D = NH₂ r₂ R = Cl, D = NH₂ p₃ R = OMe, D = NH₂ q₃ R = OMe, D = NH₂ r₃ R = OMe, D = NH₂ p₄ R = F, D = CH₂NH₂ q₄ R = F, D = CH₂NH₂ r₄ R = F, D = CH₂NH₂ p₅ R = Cl, D = CH₂NH₂ q₅ R = Cl, D = CH₂NH₂ r₅ R = Cl, D = CH₂NH₂ p₆ R = OMe, D = CH₂NH₂ q₆ R = OMe, D = CH₂NH₂ r₆ R = OMe, D = CH₂NH₂ p₇ R = F, D = C(═NH)NH₂ q₇ R = F, D = C(═NH)NH₂ r₇ R = F, D = C(═NH)NH₂ p₈ R = Cl, D = C(═NH)NH₂ q₈ R = Cl, D = C(═NH)NH₂ r₈ R = Cl, D = C(═NH)NH₂ p₉ R = OMe, D = C(═NH)NH₂ q₉ R = OMe, D = C(═NH)NH₂ r₉ R = OMe, D = C(═NH)NH₂ p₁₀ R = F, D = C(O)NH₂ q₁₀ R = F, D = C(O)NH₂ r₁₀ R = F, D = C(O)NH₂ p₁₁ R = Cl, D = C(O)NH₂ q₁₁ R = Cl, D = C(O)NH₂ r₁₁ R = Cl, D = C(O)NH₂ p₁₂ R = OMe, D = C(O)NH₂ q₁₂ R = OMe, D = C(O)NH₂ r₁₂ R = OMe, D = C(O)NH₂

s₁ R = F, D = NH₂ t₁ R = F, D = NH₂ u₁ R = F, D = NH₂ s₂ R = Cl, D = NH₂ t₂ R = Cl, D = NH₂ u₂ R = Cl, D = NH₂ s₃ R = OMe, D = NH₂ t₃ R = OMe, D = NH₂ u₃ R = OMe, D = NH₂ s₄ R = F, D = CH₂NH₂ t₄ R = F, D = CH₂NH₂ u₄ R = F, D = CH₂NH₂ s₅ R = Cl, D = CH₂NH₂ t₅ R = Cl, D = CH₂NH₂ u₅ R = Cl, D = CH₂NH₂ s₆ R = OMe, D = CH₂NH₂ t₆ R = OMe, D = CH₂NH₂ u₆ R = OMe, D = CH₂NH₂ s₇ R = F, D = C(═NH)NH₂ t₇ R = F, D = C(═NH)NH₂ u₇ R = F, D = C(═NH)NH₂ s₈ R = Cl, D = C(═NH)NH₂ t₈ R = Cl, D = C(═NH)NH₂ u₈ R = Cl, D = C(═NH)NH₂ s₉ R = OMe, D = C(═NH)NH₂ t₉ R = OMe, D = C(═NH)NH₂ u₉ R = OMe, D = C(═NH)NH₂ s₁₀ R = F, D = C(O)NH₂ t₁₀ R = F, D = C(O)NH₂ u₁₀ R = F, D = C(O)NH₂ s₁₁ R = Cl, D = C(O)NH₂ t₁₁ R = Cl, D = C(O)NH₂ u₁₁ R = Cl, D = C(O)NH₂ s₁₂ R = OMe, D = C(O)NH₂ t₁₂ R = OMe, D = C(O)NH₂ u₁₂ R = OMe, D = C(O)NH₂

v₁ R = F, D = NH₂ w₁ R = F, D = NH₂ x₁ R = F, D = NH₂ v₂ R = Cl, D = NH₂ w₂ R = Cl, D = NH₂ x₂ R = Cl, D = NH₂ v₃ R = OMe, D = NH₂ w₃ R = OMe, D = NH₂ x₃ R = OMe, D = NH₂ v₄ R = F, D = CH₂NH₂ w₄ R = F, D = CH₂NH₂ x₄ R = F, D = CH₂NH₂ v₅ R = Cl, D = CH₂NH₂ w₅ R = Cl, D = CH₂NH₂ x₅ R = Cl, D = CH₂NH₂ v₆ R = OMe, D = CH₂NH₂ w₆ R = OMe, D = CH₂NH₂ x₆ R = OMe, D = CH₂NH₂ v₇ R = F, D = C(═NH)NH₂ w₇ R = F, D = C(═NH)NH₂ x₇ R = F, D = C(═NH)NH₂ v₈ R = Cl, D = C(═NH)NH₂ w₈ R = Cl, D = C(═NH)NH₂ x₆ R = Cl, D = C(═NH)NH₂ v₉ R = OMe, D = C(═NH)NH₂ w₉ R = OMe, D = C(═NH)NH₂ x₉ R = OMe, D = C(═NH)NH₂ v₁₀ R = F, D = C(O)NH₂ w₁₀ R = F, D = C(O)NH₂ x₁₀ R = F, D = C(O)NH₂ v₁₁ R = Cl, D = C(O)NH₂ w₁₁ R = Cl, D = C(O)NH₂ x₁₁ R = Cl, D = C(O)NH₂ v₁₂ R = OMe, D = C(O)NH₂ w₁₂ R = OMe, D = C(O)NH₂ x₁₂ R = OMe, D = C(O)NH₂

y₁ R = F, D = NH₂ z₁ R = F, D = NH₂ aa₁ R = F, D = NH₂ y₂ R = Cl, D = NH₂ z₂ R = Cl, D = NH₂ aa₂ R = Cl, D = NH₂ y₃ R = OMe, D = NH₂ z₃ R = OMe, D = NH₂ aa₃ R = OMe, D = NH₂ y₄ R = F, D = CH₂NH₂ z₄ R = F, D = CH₂NH₂ aa₄ R = F, D = CH₂NH₂ y₅ R = Cl, D = CH₂NH₂ z₅ R = Cl, D = CH₂NH₂ aa₅ R = Cl, D = CH₂NH₂ y₆ R = OMe, D = CH₂NH₂ z₆ R = OMe, D = CH₂NH₂ aa₆ R = OMe, D = CH₂NH₂ y₇ R = F, D = C(═NH)NH₂ z₇ R = F, D = C(═NH)NH₂ aa₇ R = F, D = C(═NH)NH₂ y₈ R = Cl, D = C(═NH)NH₂ z₈ R = Cl, D = C(═NH)NH₂ aa₈ R = Cl, D = C(═NH)NH₂ y₉ R = OMe, D = C(═NH)NH₂ z₉ R = OMe, D = C(═NH)NH₂ aa₉ R = OMe, D = C(═NH)NH₂ y₁₀ R = F, D = C(O)NH₂ z₁₀ R = F, D = C(O)NH₂ aa₁₀ R = F, D = C(O)NH₂ y₁₁ R = Cl, D = C(O)NH₂ z₁₁ R = Cl, D = C(O)NH₂ aa₁₁ R = Cl, D = C(O)NH₂ y₁₂ R = OMe, D = C(O)NH₂ z₁₂ R = OMe, D = C(O)NH₂ aa₁₂ R = OMe, D = C(O)NH₂

bb₁ R = F, D = NH₂ cc₁ R = F, D = NH₂ dd₁ R = F, D = NH₂ bb₂ R = Cl, D = NH₂ cc₂ R = Cl, D = NH₂ dd₂ R = Cl, D = NH₂ bb₃ R = OMe, D = NH₂ cc₃ R = OMe, D = NH₂ dd₃ R = OMe, D = NH₂ bb₄ R = F, D = CH₂NH₂ cc₄ R = F, D = CH₂NH₂ dd₄ R = F, D = CH₂NH₂ bb₅ R = Cl, D = CH₂NH₂ cc₅ R = Cl, D = CH₂NH₂ dd₅ R = Cl, D = CH₂NH₂ bb₆ R = OMe, D = CH₂NH₂ cc₆ R = OMe, D = CH₂NH₂ dd₆ R = OMe, D = CH₂NH₂ bb₇ R = F, D = C(═NH)NH₂ cc₇ R = F, D = C(═NH)NH₂ dd₇ R = F, D = C(═NH)NH₂ bb₈ R = Cl, D = C(═NH)NH₂ cc₈ R = Cl, D = C(═NH)NH₂ dd₈ R = Cl, D = C(═NH)NH₂ bb₉ R = OMe, D = C(═NH)NH₂ cc₉ R = OMe, D = C(═NH)NH₂ dd₉ R = OMe, D = C(═NH)NH₂ bb₁₀ R = F, D = C(O)NH₂ cc₁₀ R = F, D = C(O)NH₂ dd₁₀ R = F, D = C(O)NH₂ bb₁₁ R = Cl, D = C(O)NH₂ cc₁₁ R = Cl, D = C(O)NH₂ dd₁₁ R = Cl, D = C(O)NH₂ bb₁₂ R = OMe, D = C(O)NH₂ cc₁₂ R = OMe, D = C(O)NH₂ dd₁₂ R = OMe, D = C(O)NH₂

ee₁ R = F, D = CH₂NH₂ ff₁ R = F, D = CH₂NH₂ gg₁ R = F, D = CH₂NH₂ ee₂ R = Cl, D = CH₂NH₂ ff₂ R = Cl, D = CH₂NH₂ gg₂ R = Cl, D = CH₂NH₂ ee₃ R = OMe, D = CH₂NH₂ ff₃ R = OMe, D = CH₂NH₂ gg₃ R = OMe, D = CH₂NH₂ ee₄ R = CH₂NH₂, D = CH₂NH₂ ff₄ R = CH₂NH₂, D = CH₂NH₂ gg₄ R = CH₂NH₂, D = CH₂NH₂

hh₁ R = F, D = CH₂NH₂ ii₁ R = F, D = CH₂NH₂ jj₁ R = F, D = CH₂NH₂ hh₂ R = Cl, D = CH₂NH₂ ii₂ R = Cl, D = CH₂NH₂ jj₂ R = Cl, D = CH₂NH₂ hh₃ R = OMe, D = CH₂NH₂ ii₃ R = OMe, D = CH₂NH₂ jj₃ R = OMe, D = CH₂NH₂ hh₄ R = CH₂NH₂, D = CH₂NH₂ ii₄ R = CH₂NH₂, D = CH₂NH₂ jj₄ R = CH₂NH₂, D = CH₂NH₂

kk₁ R = F, D = CH₂NH₂ ll₁ R = F, D = CH₂NH₂ mm₁ R = F, D = CH₂NH₂ kk₂ R = Cl, D = CH₂NH₂ ll₂ R = Cl, D = CH₂NH₂ mm₂ R = Cl, D = CH₂NH₂ kk₃ R = OMe, D = CH₂NH₂ ll₃ R = OMe, D = CH₂NH₂ mm₃ R = OMe, D = CH₂NH₂ kk₄ R = CH₂NH₂, D = CH₂NH₂ ll₄ R = CH₂NH₂, D = CH₂NH₂ mm₄ R = CH₂NH₂, D = CH₂NH₂

nn₁ R = F, D = CH₂NH₂ oo₁ R = F, D = CH₂NH₂ pp₁ R = F, D = CH₂NH₂ nn₂ R = Cl, D = CH₂NH₂ oo₂ R = Cl, D = CH₂NH₂ pp₂ R = Cl, D = CH₂NH₂ nn₃ R = OMe, D = CH₂NH₂ oo₃ R = OMe, D = CH₂NH₂ pp₃ R = OMe, D = CH₂NH₂ nn₄ R = CH₂NH₂, D = CH₂NH₂ oo₄ R = CH₂NH₂, D = CH₂NH₂ pp₄ R = CH₂NH₂, D = CH₂NH₂

qq₁ R = F, D = CH₂NH₂ rr₁ R = F, D = CH₂NH₂ ss₁ R = F, D = CH₂NH₂ qq₂ R = Cl, D = CH₂NH₂ rr₂ R = Cl, D = CH₂NH₂ ss₂ R = Cl, D = CH₂NH₂ qq₃ R = OMe, D = CH₂NH₂ rr₃ R = OMe, D = CH₂NH₂ ss₃ R = OMe, D = CH₂NH₂ qq₄ R = CH₂NH₂, D = CH₂NH₂ rr₄ R = CH₂NH₂, D = CH₂NH₂ ss₄ R = CH₂NH₂, D = CH₂NH₂ Ex # R^(1b) A B   1 H phenyl 2-(aminosulfonyl)phenyl   2 H phenyl 2-(methylaminosulfonyl)phenyl   3 H phenyl 1-pyrrolidinocarbonyl   4 H phenyl 2-(methylsulfonyl)phenyl   5 H phenyl 4-morpholino   6 H phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl   7 H phenyl 4-morpholinocarbonyl   8 H 2-pyridyl 2-(aminosulfonyl)phenyl   9 H 2-pyridyl 2-(methylaminosulfonyl)phenyl  10 H 2-pyridyl 1-pyrrolidinocarbonyl  11 H 2-pyridyl 2-(methylsulfonyl)phenyl  12 H 2-pyridyl 4-morpholino  13 H 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  14 H 2-pyridyl 4-morpholinocarbonyl  15 H 3-pyridyl 2-(aminosulfonyl)phenyl  16 H 3-pyridyl 2-(methylaminosulfonyl)phenyl  17 H 3-pyridyl 1-pyrrolidinocarbonyl  18 H 3-pyridyl 2-(methylsulfonyl)phenyl  19 H 3-pyridyl 4-morpholino  20 H 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  21 H 3-pyridyl 4-morpholinocarbonyl  22 H 2-pyrimidyl 2-(aminosulfonyl)phenyl  23 H 2-pyrimidyl 2-(methylaminosulfonyl)phenyl  24 H 2-pyrimidyl 1-pyrrolidinocarbonyl  25 H 2-pyrimidyl 2-(methylsulfonyl)phenyl  26 H 2-pyrimidyl 4-morpholino  27 H 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  28 H 2-pyrimidyl 4-morpholinocarbonyl  29 H 5-pyrimidyl 2-(aminosulfonyl)phenyl  30 H 5-pyrimidyl 2-(methylaminosulfonyl)phenyl  31 H 5-pyrimidyl 1-pyrrolidinocarbonyl  32 H 5-pyrimidyl 2-(methylsulfonyl)phenyl  33 H 5-pyrimidyl 4-morpholino  34 H 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  35 H 5-pyrimidyl 4-morpholinocarbonyl  36 H 2-Cl-phenyl 2-(aminosulfonyl)phenyl  37 H 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl  38 H 2-Cl-phenyl 1-pyrrolidinocarbonyl  39 H 2-Cl-phenyl 2-(methylsulfonyl)phenyl  40 H 2-Cl-phenyl 4-morpholino  41 H 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  42 H 2-Cl-phenyl 4-morpholinocarbonyl  43 H 2-F-phenyl 2-(aminosulfonyl)phenyl  44 H 2-F-phenyl 2-(methylaminosulfonyl)phenyl  45 H 2-F-phenyl 1-pyrrolidinocarbonyl  46 H 2-F-phenyl 2-(methylsulfonyl)phenyl  47 H 2-F-phenyl 4-morpholino  48 H 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  49 H 2-F-phenyl 4-morpholinocarbonyl  50 H 2,5-diF-phenyl 2-(aminosulfonyl)phenyl  51 H 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl  52 H 2,5-diF-phenyl 1-pyrrolidinocarbonyl  53 H 2,5-diF-phenyl 2-(methylsulfonyl)phenyl  54 H 2,5-diF-phenyl 4-morpholino  55 H 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  56 H 2,5-diF-phenyl 4-morpholinocarbonyl  57 H phenyl 2-(N-pyrrolidinyl-methyl)phenyl  58 H phenyl 2-(N-piperidinyl-methyl)phenyl  59 H phenyl 2-(N-morpholino-methyl)phenyl  60 H phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  61 H phenyl 2-(N-pyridinium-methyl)phenyl  62 H phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  63 H phenyl 2-(N-azatanyl-methyl)phenyl  64 H phenyl 2-(N-azetidinyl-methyl)phenyl  65 H phenyl 2-(N-piperazinyl-methyl)phenyl  66 H phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  67 H phenyl 2-(N-imidazolyl-methyl)phenyl  68 H phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  69 H phenyl 2-(N-pyridonyl-methyl)phenyl  70 H phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  71 H phenyl 2-(amidinyl)phenyl  72 H phenyl 2-(N-guanidinyl)phenyl  73 H phenyl 2-(imidazolyl)phenyl  74 H phenyl 2-(imidazolidinyl)phenyl  75 H phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  76 H phenyl 2-(2-pyrrolidinyl)phenyl  77 H phenyl 2-(2-piperidinyl)phenyl  78 H phenyl 2-(amidinyl-methyl)phenyl  79 H phenyl 2-(2-imidazolidinyl-methyl)phenyl  80 H phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  81 H phenyl 2-dimethylaminoimidazol-1-yl  82 H phenyl 2-(3-aminophenyl)  83 H phenyl 2-(3-pyrrolidinylcarbonyl)  84 H phenyl 2-glycinoyl  85 H phenyl 2-(imidazol-1-ylacetyl)  86 H 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl  87 H 2-pyridyl 2-(N-piperidinyl-methyl)phenyl  88 H 2-pyridyl 2-(N-morpholino-methyl)phenyl  89 H 2-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl  90 H 2-pyridyl 2-(N-pyridinium-methyl)phenyl  91 H 2-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  92 H 2-pyridyl 2-(N-azatanyl-methyl)phenyl  93 H 2-pyridyl 2-(N-azetidinyl-methyl)phenyl  94 H 2-pyridyl 2-(N-piperazinyl-methyl)phenyl  95 H 2-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  96 H 2-pyridyl 2-(N-imidazolyl-methyl)phenyl  97 H 2-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl  98 H 2-pyridyl 2-(N-pyridonyl-methyl)phenyl  99 H 2-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  100 H 2-pyridyl 2-(amidinyl)phenyl  101 H 2-pyridyl 2-(N-guanidinyl)phenyl  102 H 2-pyridyl 2-(imidazolyl)phenyl  103 H 2-pyridyl 2-(imidazolidinyl)phenyl  104 H 2-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl  105 H 2-pyridyl 2-(2-pyrrolidinyl)phenyl  106 H 2-pyridyl 2-(2-piperidinyl)phenyl  107 H 2-pyridyl 2-(amidinyl-methyl)phenyl  108 H 2-pyridyl 2-(2-imidazolidinyl-methyl)phenyl  109 H 2-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  110 H 2-pyridyl 2-dimethylaminoimidazol-1-yl  111 H 2-pyridyl 2-(3-aminophenyl)  112 H 2-pyridyl 2-(3-pyrrolidinylcarbonyl)  113 H 2-pyridyl 2-glycinoyl  114 H 2-pyridyl 2-(imidazol-1-ylacetyl)  115 H 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl  116 H 3-pyridyl 2-(N-piperidinyl-methyl)phenyl  117 H 3-pyridyl 2-(N-morpholino-methyl)phenyl  118 H 3-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl  119 H 3-pyridyl 2-(N-pyridinium-methyl)phenyl  120 H 3-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  121 H 3-pyridyl 2-(N-azatanyl-methyl)phenyl  122 H 3-pyridyl 2-(N-azetidinyl-methyl)phenyl  123 H 3-pyridyl 2-(N-piperazinyl-methyl)phenyl  124 H 3-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  125 H 3-pyridyl 2-(N-imidazolyl-methyl)phenyl  126 H 3-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl  127 H 3-pyridyl 2-(N-pyridonyl-methyl)phenyl  128 H 3-pyridyl 2-(N-(N′,N-dimethylhydrazinyl-methyl)phenyl  129 H 3-pyridyl 2-(amidinyl)phenyl  130 H 3-pyridyl 2-(N-guanidinyl)phenyl  131 H 3-pyridyl 2-(imidazolyl)phenyl  132 H 3-pyridyl 2-(imidazolidinyl)phenyl  133 H 3-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl  134 H 3-pyridyl 2-(2-pyrrolidinyl)phenyl  135 H 3-pyridyl 2-(2-piperidinyl)phenyl  136 H 3-pyridyl 2-(amidinyl-methyl)phenyl  137 H 3-pyridyl 2-(2-imidazolidinyl-methyl)phenyl  138 H 3-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  139 H 3-pyridyl 2-dimethylaminoimidazol-1-yl  140 H 3-pyridyl 2-(3-aminophenyl)  141 H 3-pyridyl 2-(3-pyrrolidinylcarbonyl)  142 H 3-pyridyl 2-glycinoyl  143 H 3-pyridyl 2-(imidazol-1-ylacetyl)  144 H 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl  145 H 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl  146 H 2-pyrimidyl 2-(N-morpholino-methyl)phenyl  147 H 2-pyrimidyl 2-(N,N′-methylmorpholinium-methyl)phenyl  148 H 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl  149 H 2-pyrimidyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  150 H 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl  151 H 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl  152 H 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl  153 H 2-pyrimidyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  154 H 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl  155 H 2-pyrimidyl 2-(N-methoxy-N-methylamino-methyl)phenyl  156 H 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl  157 H 2-pyrimidyl 2-(N-(N,N′-dimethylhydrazinyl-methyl)phenyl  158 H 2-pyrimidyl 2-(amidinyl)phenyl  159 H 2-pyrimidyl 2-(N-guanidinyl)phenyl  160 H 2-pyrimidyl 2-(imidazolyl)phenyl  161 H 2-pyrimidyl 2-(imidazolidinyl)phenyl  162 H 2-pyrimidyl 2-(2-imidazolidinyl-sulfonyl)phenyl  163 H 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl  164 H 2-pyrimidyl 2-(2-piperidinyl)phenyl  165 H 2-pyrimidyl 2-(amidinyl-methyl)phenyl  166 H 2-pyrimidyl 2-(2-imidazolidinyl-methyl)phenyl  167 H 2-pyrimidyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  168 H 2-pyrimidyl 2-dimethylaminoimidazol-1-yl  169 H 2-pyrimidyl 2-(3-aminophenyl)  170 H 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl)  171 H 2-pyrimidyl 2-glycinoyl  172 H 2-pyrimidyl 2-(imidazol-1-ylacetyl)  173 H 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  174 H 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl  175 H 2-Cl-phenyl 2-(N-morpho1ino-methyl)phenyl  176 H 2-Cl-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  177 H 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl  178 H 2-Cl-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  179 H 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl  180 H 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl  181 H 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl  182 H 2-Cl-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  183 H 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl  184 H 2-Cl-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  185 H 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl  186 H 2-Cl-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  187 H 2-Cl-phenyl 2-(amidinyl)phenyl  188 H 2-Cl-phenyl 2-(N-guanidinyl)phenyl  189 H 2-Cl-phenyl 2-(imidazolyl)phenyl  190 H 2-Cl-phenyl 2-(imidazolidinyl)phenyl  191 H 2-Cl-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  192 H 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl  193 H 2-Cl-phenyl 2-(2-piperidinyl)phenyl  194 H 2-Cl-phenyl 2-(amidinyl-methyl)phenyl  195 H 2-Cl-phenyl 2-(2-imidazolidinyl-methyl)phenyl  196 H 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  197 H 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl  198 H 2-Cl-phenyl 2-(3-aminophenyl)  199 H 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl)  200 H 2-Cl-phenyl 2-glycinoyl  201 H 2-Cl-phenyl 2-(imidazol-1-ylacetyl)  202 H 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  203 H 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl  204 H 2-F-phenyl 2-(N-morpholino-methyl)phenyl  205 H 2-F-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  206 H 2-F-phenyl 2-(N-pyridinium-methyl)phenyl  207 H 2-F-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  208 H 2-F-phenyl 2-(N-azatanyl-methyl)phenyl  209 H 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl  210 H 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl  211 H 2-F-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  212 H 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl  213 H 2-F-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  214 H 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl  215 H 2-F-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  216 H 2-F-phenyl 2-(amidinyl)phenyl  217 H 2-F-phenyl 2-(N-guanidinyl)phenyl  218 H 2-F-phenyl 2-(imidazolyl)phenyl  219 H 2-F-phenyl 2-(imidazolidinyl)phenyl  220 H 2-F-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  221 H 2-F-phenyl 2-(2-pyrrolidinyl)phenyl  222 H 2-F-phenyl 2-(2-piperidinyl)phenyl  223 H 2-F-phenyl 2-(amidinyl-methyl)phenyl  224 H 2-F-phenyl 2-(2-imidazolidinyl-methyl)phenyl  225 H 2-F-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  226 H 2-F-phenyl 2-dimethylaminoimidazol-1-yl  227 H 2-F-phenyl 2-(3-aminophenyl)  228 H 2-F-phenyl 2-(3-pyrrolidinylcarbonyl)  229 H 2-F-phenyl 2-glycinoyl  230 H 2-F-phenyl 2-(imidazol-1-ylacetyl)  231 H 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  232 H 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl  233 H 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl  234 H 2,5-diF-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  235 H 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl  236 H 2,5-diF-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  237 H 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl  238 H 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl  239 H 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl  240 H 2,5-diF-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  241 H 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl  242 H 2,5-diF-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  243 H 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl  244 H 2,5-diF-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  245 H 2,5-diF-phenyl 2-(amidinyl)phenyl  246 H 2,5-diF-phenyl 2-(N-guanidinyl)phenyl  247 H 2,5-diF-phenyl 2-(imidazolyl)phenyl  248 H 2,5-diF-phenyl 2-(imidazolidinyl)phenyl  249 H 2,5-diF-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  250 H 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl  251 H 2,5-diF-phenyl 2-(2-piperidinyl)phenyl  252 H 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl  253 H 2,5-diF-phenyl 2-(2-imidazolidinyl-methyl)phenyl  254 H 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  255 H 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl  256 H 2,5-diF-phenyl 2-(3-aminophenyl)  257 H 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl)  258 H 2,5-diF-phenyl 2-glycinoyl  259 H 2,5-diF-phenyl 2-(imidazol-1-ylacetyl)  260 —CN phenyl 2-(aminosulfonyl)phenyl  261 —CN phenyl 2-(methylaminosulfonyl)phenyl  262 —CN phenyl 1-pyrrolidinocarbonyl  263 —CN phenyl 2-(methylsulfonyl)phenyl  264 —CN phenyl 4-morpholino  265 —CN phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  266 —CN phenyl 4-morpholinocarbonyl  267 —CN 2-pyridyl 2-(aminosulfonyl)phenyl  268 —CN 2-pyridyl 2-(methylaminosulfonyl)phenyl  269 —CN 2-pyridyl 1-pyrrolidinocarbonyl  270 —CN 2-pyridyl 2-(methylsulfonyl)phenyl  271 —CN 2-pyridyl 4-morpholino  272 —CN 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  273 —CN 2-pyridyl 4-morpholinocarbonyl  274 —CN 3-pyridyl 2-(aminosulfonyl)phenyl  275 —CN 3-pyridyl 2-(methylaminosulfonyl)phenyl  276 —CN 3-pyridyl 1-pyrrolidinocarbonyl  277 —CN 3-pyridyl 2-(methylsulfonyl)phenyl  278 —CN 3-pyridyl 4-morpholino  279 —CN 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  280 —CN 3-pyridyl 4-morpholinocarbonyl  281 —CN 2-pyrimidyl 2-(aminosulfonyl)phenyl  282 —CN 2-pyrimidyl 2-(methylaminosulfonyl)phenyl  283 —CN 2-pyrimidyl 1-pyrrolidinocarbonyl  284 —CN 2-pyrimidyl 2-(methylsulfonyl)phenyl  285 —CN 2-pyrimidyl 4-morpholino  286 —CN 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  287 —CN 2-pyrimidyl 4-morpholinocarbonyl  288 —CN 5-pyrimidyl 2-(aminosulfonyl)phenyl  289 —CN 5-pyrimidyl 2-(methylaminosulfonyl)phenyl  290 —CN 5-pyrimidyl 1-pyrrolidinocarbonyl  291 —CN 5-pyrimidyl 2-(methylsulfonyl)phenyl  292 —CN 5-pyrimidyl 4-morpholino  293 —CN 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  294 —CN 5-pyrimidyl 4-morpholinocarbonyl  295 —CN 2-Cl-phenyl 2-(aminosulfonyl)phenyl  296 —CN 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl  297 —CN 2-Cl-phenyl 1-pyrrolidinocarbonyl  298 —CN 2-Cl-phenyl 2-(methylsulfonyl)phenyl  299 —CN 2-Cl-phenyl 4-morpholino  300 —CN 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  301 —CN 2-Cl-phenyl 4-morpholinocarbonyl  302 —CN 2-F-phenyl 2-(aminosulfonyl)phenyl  303 —CN 2-F-phenyl 2-(methylaminosulfonyl)phenyl  304 —CN 2-F-phenyl 1-pyrrolidinocarbonyl  305 —CN 2-F-phenyl 2-(methylsulfonyl)phenyl  306 —CN 2-F-phenyl 4-morpholino  307 —CN 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  308 —CN 2-F-phenyl 4-morpholinocarbonyl  309 —CN 2,5-diF-phenyl 2-(aminosulfonyl)phenyl  310 —CN 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl  311 —CN 2,5-diF-phenyl 1-pyrrolidinocarbonyl  312 —CN 2,5-diF-phenyl 2-(methylsulfonyl)phenyl  313 —CN 2,5-diF-phenyl 4-morpholino  314 —CN 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  315 —CN 2,5-diF-phenyl 4-morpholinocarbonyl  316 —CN phenyl 2-(N-pyrrolidinyl-methyl)phenyl  317 —CN phenyl 2-(N-piperidinyl-methyl)phenyl  318 —CN phenyl 2-(N-morpholino-methyl)phenyl  319 —CN phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  320 —CN phenyl 2-(N-pyridinium-methyl)phenyl  321 —CN phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  322 —CN phenyl 2-(N-azatanyl-methyl)phenyl  323 —CN phenyl 2-(N-azetidinyl-methyl)phenyl  324 —CN phenyl 2-(N-piperazinyl-methyl)phenyl  325 —CN phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  326 —CN phenyl 2-(N-imidazolyl-methyl)phenyl  327 —CN phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  328 —CN phenyl 2-(N-pyridonyl-methyl)phenyl  329 —CN phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  330 —CN phenyl 2-(amidinyl)phenyl  331 —CN phenyl 2-(N-guanidinyl)phenyl  332 —CN phenyl 2-(imidazolyl)phenyl  333 —CN phenyl 2-(imidazolidinyl)phenyl  334 —CN phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  335 —CN phenyl 2-(2-pyrrolidinyl)phenyl  336 —CN phenyl 2-(2-piperidinyl)phenyl  337 —CN phenyl 2-(amidinyl-methyl)phenyl  338 —CN phenyl 2-(2-imidazolidinyl-methyl)phenyl  339 —CN phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  340 —CN phenyl 2-dimethylaminoimidazol-1-yl  341 —CN phenyl 2-(3-aminophenyl)  342 —CN phenyl 2-(3-pyrrolidinylcarbonyl)  343 —CN phenyl 2-glycinoyl  344 —CN phenyl 2-(imidazol-1-ylacetyl)  345 —CN 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl  346 —CN 2-pyridyl 2-(N-piperidinyl-methyl)phehyl  347 —CN 2-pyridyl 2-(N-morpholino-methyl)phenyl  348 —CN 2-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl  349 —CN 2-pyridyl 2-(N-pyridinium-methyl)phenyl  350 —CN 2-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  351 —CN 2-pyridyl 2-(N-azatanyl-methyl)phenyl  352 —CN 2-pyridyl 2-(N-azetidinyl-methyl)phenyl  353 —CN 2-pyridyl 2-(N-piperazinyl-methyl)phenyl  354 —CN 2-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  355 —CN 2-pyridyl 2-(N-imidazolyl-methyl)phenyl  356 —CN 2-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl  357 —CN 2-pyridyl 2-(N-pyridonyl-methyl)phenyl  358 —CN 2-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  359 —CN 2-pyridyl 2-(amidinyl)phenyl  360 —CN 2-pyridyl 2-(N-guanidinyl)phenyl  361 —CN 2-pyridyl 2-(imidazolyl)phenyl  362 —CN 2-pyridyl 2-(imidazolidinyl)phenyl  363 —CN 2-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl  364 —CN 2-pyridyl 2-(2-pyrrolidinyl)phenyl  365 —CN 2-pyridyl 2-(2-piperidinyl)phenyl  366 —CN 2-pyridyl 2-(amidinyl-methyl)phenyl  367 —CN 2-pyridyl 2-(2-imidazolidinyl-methyl)phenyl  368 —CN 2-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  369 —CN 2-pyridyl 2-dimethylaminoimidazol-1-yl  370 —CN 2-pyridyl 2-(3-aminophenyl)  371 —CN 2-pyridyl 2-(3-pyrrolidinylcarbonyl)  372 —CN 2-pyridyl 2-glycinoyl  373 —CN 2-pyridyl 2-(imidazol-1-ylacetyl)  374 —CN 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl  375 —CN 3-pyridyl 2-(N-piperidinyl-methyl)phenyl  376 —CN 3-pyridyl 2-(N-morpholino-methyl)phenyl  377 —CN 3-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl  378 —CN 3-pyridyl 2-(N-pyridinium-methyl)phenyl  379 —CN 3-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  380 —CN 3-pyridyl 2-(N-azatanyl-methyl)phenyl  381 —CN 3-pyridyl 2-(N-azetidinyl-methyl)phenyl  382 —CN 3-pyridyl 2-(N-piperazinyl-methyl)phenyl  383 —CN 3-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  384 —CN 3-pyridyl 2-(N-imidazolyl-methyl)phenyl  385 —CN 3-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl  386 —CN 3-pyridyl 2-(N-pyridonyl-methyl)phenyl  387 —CN 3-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  388 —CN 3-pyridyl 2-(amidinyl)phenyl  389 —CN 3-pyridyl 2-(N-guanidinyl)phenyl  390 —CN 3-pyridyl 2-(imidazolyl)phenyl  391 —CN 3-pyridyl 2-(imidazolidinyl)phenyl  392 —CN 3-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl  393 —CN 3-pyridyl 2-(2-pyrrolidinyl)phenyl  394 —CN 3-pyridyl 2-(2-piperidinyl)phenyl  395 —CN 3-pyridyl 2-(amidinyl-methyl)phenyl  396 —CN 3-pyridyl 2-(2-imidazolidinyl-methyl)phenyl  397 —CN 3-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  398 —CN 3-pyridyl 2-dimethylaminoimidazol-1-yl  399 —CN 3-pyridyl 2-(3-aminophenyl)  400 —CN 3-pyridyl 2-(3-pyrrolidinylcarbonyl)  401 —CN 3-pyridyl 2-glycinoyl  402 —CN 3-pyridyl 2-(imidazol-1-ylacetyl)  403 —CN 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl  404 —CN 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl  405 —CN 2-pyrimidyl 2-(N-morpholino-methyl)phenyl  406 —CN 2-pyrimidyl 2-(N,N′-methylmorpholinium-methyl)phenyl  407 —CN 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl  408 —CN 2-pyrimidyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  409 —CN 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl  410 —CN 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl  411 —CN 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl  412 —CN 2-pyrimidyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  413 —CN 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl  414 —CN 2-pyrimidyl 2-(N-methoxy-N-methylamino-methyl)phenyl  415 —CN 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl  416 —CN 2-pyrimidyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  417 —CN 2-pyrimidyl 2-(amidinyl)phenyl  418 —CN 2-pyrimidyl 2-(N-guanidinyl)phenyl  419 —CN 2-pyrimidyl 2-(imidazolyl)phenyl  420 —CN 2-pyrimidyl 2-(imidazolidinyl)phenyl  421 —CN 2-pyrimidyl 2-(2-imidazolidinyl-sulfonyl)phenyl  422 —CN 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl  423 —CN 2-pyrimidyl 2-(2-piperidinyl)phenyl  424 —CN 2-pyrimidyl 2-(amidinyl-methyl)phenyl  425 —CN 2-pyrimidyl 2-(2-imidazolidinyl-methyl)phenyl  426 —CN 2-pyrimidyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  427 —CN 2-pyrimidyl 2-dimethylaminoimidazol-1-yl  428 —CN 2-pyrimidyl 2-(3-aminophenyl)  429 —CN 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl)  430 —CN 2-pyrimidyl 2-glycinoyl  431 —CN 2-pyrimidyl 2-(imidazol-1-ylacetyl)  432 —CN 2-Cl-phenyl 2-(N-Pyrrolidinyl-methyl)phenyl  433 —CN 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl  434 —CN 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl  435 —CN 2-Cl-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  436 —CN 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl  437 —CN 2-Cl-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  438 —CN 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl  439 —CN 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl  440 —CN 2-Cl-phenyl 2-(N-piperazinyl-methyl)phehyl  441 —CN 2-Cl-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  442 —CN 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl  443 —CN 2-Cl-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  444 —CN 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl  445 —CN 2-Cl-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  446 —CN 2-Cl-phenyl 2-(amidinyl)phenyl  447 —CN 2-Cl-phenyl 2-(N-guanidinyl)phenyl  448 —CN 2-Cl-phenyl 2-(imidazolyl)phenyl  449 —CN 2-Cl-phenyl 2-(imidazolidinyl)phenyl  450 —CN 2-Cl-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  451 —CN 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl  452 —CN 2-Cl-phenyl 2-(2-piperidinyl)phenyl  453 —CN 2-Cl-phenyl 2-(amidinyl-methyl)phenyl  454 —CN 2-Cl-phenyl 2-(2-imidazolidinyl-methyl)phenyl  455 —CN 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  456 —CN 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl  457 —CN 2-Cl-phenyl 2-(3-aminophenyl)  458 —CN 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl)  459 —CN 2-Cl-phenyl 2-glycinoyl  460 —CN 2-Cl-phenyl 2-(imidazol-1-ylacetyl)  461 —CN 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  462 —CN 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl  463 —CN 2-F-phenyl 2-(N-morpholino-methyl)phenyl  464 —CN 2-F-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  465 —CN 2-F-phenyl 2-(N-pyridinium-methyl)phenyl  466 —CN 2-F-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  467 —CN 2-F-phenyl 2-(N-azatanyl-methyl)phenyl  468 —CN 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl  469 —CN 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl  470 —CN 2-F-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  471 —CN 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl  472 —CN 2-F-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  473 —CN 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl  474 —CN 2-F-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  475 —CN 2-F-phenyl 2-(amidinyl)phenyl  476 —CN 2-F-phenyl 2-(N-guanidinyl)phenyl  477 —CN 2-F-phenyl 2-(imidazolyl)phenyl  478 —CN 2-F-phenyl 2-(imidazolidinyl)phenyl  479 —CN 2-F-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  480 —CN 2-F-phenyl 2-(2-pyrrolidinyl)phenyl  481 —CN 2-F-phenyl 2-(2-piperidinyl)phenyl  482 —CN 2-F-phenyl 2-(amidinyl-methyl)phenyl  483 —CN 2-F-phenyl 2-(2-imidazolidinyl-methyl)phenyl  484 —CN 2-F-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  485 —CN 2-F-phenyl 2-dimethylaminoimidazol-1-yl  486 —CN 2-F-phenyl 2-(3-aminophenyl)  487 —CN 2-F-phenyl 2-(3-pyrrolidinylcarbonyl)  488 —CN 2-F-phenyl 2-glycinoyl  489 —CN 2-F-phenyl 2-(imidazol-1-ylacetyl)  490 —CN 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  491 —CN 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl  492 —CN 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl  493 —CN 2,5-diF-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  494 —CN 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl  495 —CN 2,5-diF-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  496 —CN 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl  497 —CN 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl  498 —CN 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl  499 —CN 2,5-diF-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  500 —CN 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl  501 —CN 2,5-diF-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  502 —CN 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl  503 —CN 2,5-diF-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  504 —CN 2,5-diF-phenyl 2-(amidinyl)phenyl  505 —CN 2,5-diF-phenyl 2-(N-guanidinyl)phenyl  506 —CN 2,5-diF-phenyl 2-(imidazolyl)phenyl  507 —CN 2,5-diF-phenyl 2-(imidazolidinyl)phenyl  508 —CN 2,5-diF-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  509 —CN 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl  510 —CN 2,5-diF-phenyl 2-(2-piperidinyl)phenyl  511 —CN 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl  512 —CN 2,5-diF-phenyl 2-(2-imidazolidinyl-methyl)phenyl  513 —CN 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  514 —CN 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl  515 —CN 2,5-diF-phenyl 2-(3-aminophenyl)  516 —CN 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl)  517 —CN 2,5-diF-phenyl 2-glycinoyl  518 —CN 2,5-diF-phenyl 2-(imidazol-1-ylacetyl)  519 CF₃ phenyl 2-(aminosulfonyl)phenyl  520 CF₃ phenyl 2-(methylaminosulfonyl)phenyl  521 CF₃ phenyl 1-pyrrolidinocarbonyl  522 CF₃ phenyl 2-(methylsulfonyl)phenyl  523 CF₃ phenyl 4-morpholino  524 CF₃ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  525 CF₃ phenyl 4-morpholinocarbonyl  526 CF₃ 2-pyridyl 2-(aminosulfonyl)phenyl  527 CF₃ 2-pyridyl 2-(methylaminosulfonyl)phenyl  528 CF₃ 2-pyridyl 1-pyrrolidinocarbonyl  529 CF₃ 2-pyridyl 2-(methylsulfonyl)phenyl  530 CF₃ 2-pyridyl 4-morpholino  531 CF₃ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  532 CF₃ 2-pyridyl 4-morpholinocarbonyl  533 CF₃ 3-pyridyl 2-(aminosulfonyl)phenyl  534 CF₃ 3-pyridyl 2-(methylaminosulfonyl)phenyl  535 CF₃ 3-pyridyl 1-pyrrolidinocarbonyl  536 CF₃ 3-pyridyl 2-(methylsulfonyl)phenyl  537 CF₃ 3-pyridyl 4-morpholino  538 CF₃ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  539 CF₃ 3-pyridyl 4-morpholinocarbonyl  540 CF₃ 2-pyrimidyl 2-(aminosulfonyl)phenyl  541 CF₃ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl  542 CF₃ 2-pyrimidyl 1-pyrrolidinocarbonyl  543 CF₃ 2-pyrimidyl 2-(methylsulfonyl)phenyl  544 CF₃ 2-pyrimidyl 4-morpholino  545 CF₃ 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  546 CF₃ 2-pyrimidyl 4-morpholinocarbonyl  547 CF₃ 5-pyrimidyl 2-(aminosulfonyl)phenyl  548 CF₃ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl  549 CF₃ 5-pyrimidyl 1-pyrrolidinocarbonyl  550 CF₃ 5-pyrimidyl 2-(methylsulfonyl)phenyl  551 CF₃ 5-pyrimidyl 4-morpholino  552 CF₃ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  553 CF₃ 5-pyrimidyl 4-morpholinocarbonyl  554 CF₃ 2-Cl-phenyl 2-(aminosulfonyl)phenyl  555 CF₃ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl  556 CF₃ 2-Cl-phenyl 1-pyrrolidinocarbonyl  557 CF₃ 2-Cl-phenyl 2-(methylsulfonyl)phenyl  558 CF₃ 2-Cl-phenyl 4-morpholino  559 CF₃ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  560 CF₃ 2-Cl-phenyl 4-morpholinocarbonyl  561 CF₃ 2-F-phenyl 2-(aminosulfonyl)phenyl  562 CF₃ 2-F-phenyl 2-(methylaminosulfonyl)phenyl  563 CF₃ 2-F-phenyl 1-pyrrolidinocarbonyl  564 CF₃ 2-F-phenyl 2-(methylsulfonyl)phenyl  565 CF₃ 2-F-phenyl 4-morpholino  566 CF₃ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  567 CF₃ 2-F-phenyl 4-morpholinocarbonyl  568 CF₃ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl  569 CF₃ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl  570 CF₃ 2,5-diF-phenyl 1-pyrrolidinocarbonyl  571 CF₃ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl  572 CF₃ 2,5-diF-phenyl 4-morpholino  573 CF₃ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  574 CF₃ 2,5-diF-phenyl 4-morpholinocarbonyl  575 CF₃ phenyl 2-(N-pyrrolidinyl-methyl)phenyl  576 CF₃ phenyl 2-(N-piperidinyl-methyl)phenyl  577 CF₃ phenyl 2-(N-morpholino-methyl)phenyl  578 CF₃ phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  579 CF₃ phenyl 2-(N-pyridinium-methyl)phenyl  580 CF₃ phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  581 CF₃ phenyl 2-(N-azatanyl-methyl)phenyl  582 CF₃ phenyl 2-(N-azetidinyl-methyl)phenyl  583 CF₃ phenyl 2-(N-piperazinyl-methyl)phenyl  584 CF₃ phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  585 CF₃ phenyl 2-(N-imidazolyl-methyl)phenyl  586 CF₃ phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  587 CF₃ phenyl 2-(N-pyridonyl-methyl)phenyl  588 CF₃ phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  589 CF₃ phenyl 2-(amidinyl)phenyl  590 CF₃ phenyl 2-(N-guanidinyl)phenyl  591 CF₃ phenyl 2-(imidazolyl)phenyl  592 CF₃ phenyl 2-(imidazolidinyl)phenyl  593 CF₃ phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  594 CF₃ phenyl 2-(2-pyrrolidinyl)phenyl  595 CF₃ phenyl 2-(2-piperidinyl)phenyl  596 CF₃ phenyl 2-(amidinyl-methyl)phenyl  597 CF₃ phenyl 2-(2-imidazolidinyl-methyl)phenyl  598 CF₃ phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  599 CF₃ phenyl 2-dimethylaminoimidazol-1-yl  600 CF₃ phenyl 2-(3-aminophenyl)  601 CF₃ phenyl 2-(3-pyrrolidinylcarbonyl)  602 CF₃ phenyl 2-glycinoyl  603 CF₃ phenyl 2-(imidazol-1-ylacetyl)  604 CF₃ 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl  605 CF₃ 2-pyridyl 2-(N-piperidinyl-methyl)phenyl  606 CF₃ 2-pyridyl 2-(N-morpholino-methyl)phenyl  607 CF₃ 2-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl  608 CF₃ 2-pyridyl 2-(N-pyridinium-methyl)phenyl  609 CF₃ 2-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  610 CF₃ 2-pyridyl 2-(N-azatanyl-methyl)phenyl  611 CF₃ 2-pyridyl 2-(N-azetidinyl-methyl)phenyl  612 CF₃ 2-pyridyl 2-(N-piperazinyl-methyl)phenyl  613 CF₃ 2-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  614 CF₃ 2-pyridyl 2-(N-imidazolyl-methyl)phenyl  615 CF₃ 2-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl  616 CF₃ 2-pyridyl 2-(N-pyridonyl-methyl)phenyl  617 CF₃ 2-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  618 CF₃ 2-pyridyl 2-(amidinyl)phenyl  619 CF₃ 2-pyridyl 2-(N-guanidinyl)phenyl  620 CF₃ 2-pyridyl 2-(imidazolyl)phenyl  621 CF₃ 2-pyridyl 2-(imidazolidinyl)phenyl  622 CF₃ 2-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl  623 CF₃ 2-pyridyl 2-(2-pyrrolidinyl)phenyl  624 CF₃ 2-pyridyl 2-(2-piperidinyl)phenyl  625 CF₃ 2-pyridyl 2-(amidinyl-methyl)phenyl  626 CF₃ 2-pyridyl 2-(2-imidazolidinyl-methyl)phenyl  627 CF₃ 2-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  628 CF₃ 2-pyridyl 2-dimethylaminoimidazol-1-yl  629 CF₃ 2-pyridyl 2-(3-aminophenyl)  630 CF₃ 2-pyridyl 2-(3-pyrrolidinylcarbonyl)  631 CF₃ 2-pyridyl 2-glycinoyl  632 CF₃ 2-pyridyl 2-(imidazol-1-ylacetyl)  633 CF₃ 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl  634 CF₃ 3-pyridyl 2-(N-piperidinyl-methyl)phenyl  635 CF₃ 3-pyridyl 2-(N-morpholino-methyl)phenyl  636 CF₃ 3-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl  637 CF₃ 3-pyridyl 2-(N-pyridinium-methyl)phenyl  638 CF₃ 3-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  639 CF₃ 3-pyridyl 2-(N-azatanyl-methyl)phenyl  640 CF₃ 3-pyridyl 2-(N-azetidinyl-methyl)phenyl  641 CF₃ 3-pyridyl 2-(N-piperazinyl-methyl)phenyl  642 CF₃ 3-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  643 CF₃ 3-pyridyl 2-(N-imidazolyl-methyl)phenyl  644 CF₃ 3-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl  645 CF₃ 3-pyridyl 2-(N-pyridonyl-methyl)phenyl  646 CF₃ 3-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  647 CF₃ 3-pyridyl 2-(amidinyl)phenyl  648 CF₃ 3-pyridyl 2-(N-guanidinyl)phenyl  649 CF₃ 3-pyridyl 2-(imidazolyl)phenyl  650 CF₃ 3-pyridyl 2-(imidazolidinyl)phenyl  651 CF₃ 3-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl  652 CF₃ 3-pyridyl 2-(2-pyrrolidinyl)phenyl  653 CF₃ 3-pyridyl 2-(2-piperidinyl)phenyl  654 CF₃ 3-pyridyl 2-(amidinyl-methyl)phenyl  655 CF₃ 3-pyridyl 2-(2-imidazolidinyl-methyl)phenyl  656 CF₃ 3-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  657 CF₃ 3-pyridyl 2-dimethylaminoimidazol-1-yl  658 CF₃ 3-pyridyl 2-(3-aminophenyl)  659 CF₃ 3-pyridyl 2-(3-pyrrolidinylcarbonyl)  660 CF₃ 3-pyridyl 2-glycinoyl  661 CF₃ 3-pyridyl 2-(imidazol-1-ylacetyl)  662 CF₃ 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl  663 CF₃ 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl  664 CF₃ 2-pyrimidyl 2-(N-morpholino-methyl)phenyl  665 CF₃ 2-pyrimidyl 2-(N,N′-methylmorpholinium-methyl)phenyl  666 CF₃ 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl  667 CF₃ 2-pyrimidyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  668 CF₃ 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl  669 CF₃ 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl  670 CF₃ 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl  671 CF₃ 2-pyrimidyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  672 CF₃ 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl  673 CF₃ 2-pyrimidyl 2-(N-methoxy-N-methylamino-methyl)phenyl  674 CF₃ 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl  675 CF₃ 2-pyrimidyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  676 CF₃ 2-pyrimidyl 2-(amidinyl)phenyl  677 CF₃ 2-pyrimidyl 2-(N-guanidinyl)phenyl  678 CF₃ 2-pyrimidyl 2-(imidazolyl)phenyl  679 CF₃ 2-pyrimidyl 2-(imidazolidinyl)phenyl  680 CF₃ 2-pyrimidyl 2-(2-imidazolidinyl-sulfonyl)phenyl  681 CF₃ 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl  682 CF₃ 2-pyrimidyl 2-(2-piperidinyl)phenyl  683 CF₃ 2-pyrimidyl 2-(amidinyl-methyl)phenyl  684 CF₃ 2-pyrimidyl 2-(2-imidazolidinyl-methyl)phenyl  685 CF₃ 2-pyrimidyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  686 CF₃ 2-pyrimidyl 2-dimethylaminoimidazol-1-yl  687 CF₃ 2-pyrimidyl 2-(3-aminophenyl)  688 CF₃ 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl)  689 CF₃ 2-pyrimidyl 2-glycinoyl  690 CF₃ 2-pyrimidyl 2-(imidazol-1-ylacetyl)  691 CF₃ 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  692 CF₃ 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl  693 CF₃ 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl  694 CF₃ 2-Cl-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  695 CF₃ 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl  696 CF₃ 2-Cl-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  697 CF₃ 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl  698 CF₃ 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl  699 CF₃ 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl  700 CF₃ 2-Cl-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  701 CF₃ 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl  702 CF₃ 2-Cl-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  703 CF₃ 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl  704 CF₃ 2-Cl-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  705 CF₃ 2-Cl-phenyl 2-(amidinyl)phenyl  706 CF₃ 2-Cl-phenyl 2-(N-guanidinyl)phenyl  707 CF₃ 2-Cl-phenyl 2-(imidazolyl)phenyl  708 CF₃ 2-Cl-phenyl 2-(imidazolidinyl)phenyl  709 CF₃ 2-Cl-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  710 CF₃ 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl  711 CF₃ 2-Cl-phenyl 2-(2-piperidinyl)phenyl  712 CF₃ 2-Cl-phenyl 2-(amidinyl-methyl)phenyl  713 CF₃ 2-Cl-phenyl 2-(2-imidazolidinyl-methyl)phenyl  714 CF₃ 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  715 CF₃ 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl  716 CF₃ 2-Cl-phenyl 2-(3-aminophenyl)  717 CF₃ 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl)  718 CF₃ 2-Cl-phenyl 2-glycinoyl  719 CF₃ 2-Cl-phenyl 2-(imidazol-1-ylacetyl)  720 CF₃ 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  721 CF₃ 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl  722 CF₃ 2-F-phenyl 2-(N-morpholino-methyl)phenyl  723 CF₃ 2-F-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  724 CF₃ 2-F-phenyl 2-(N-pyridinium-methyl)phenyl  725 CF₃ 2-F-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  726 CF₃ 2-F-phenyl 2-(N-azatanyl-methyl)phenyl  727 CF₃ 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl  728 CF₃ 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl  729 CF₃ 2-F-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  730 CF₃ 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl  731 CF₃ 2-F-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  732 CF₃ 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl  733 CF₃ 2-F-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  734 CF₃ 2-F-phenyl 2-(amidinyl)phenyl  735 CF₃ 2-F-phenyl 2-(N-guanidinyl)phenyl  736 CF₃ 2-F-phenyl 2-(imidazolyl)phenyl  737 CF₃ 2-F-phenyl 2-(imidazolidinyl)phenyl  738 CF₃ 2-F-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  739 CF₃ 2-F-phenyl 2-(2-pyrrolidinyl)phenyl  740 CF₃ 2-F-phenyl 2-(2-piperidinyl)phenyl  741 CF₃ 2-F-phenyl 2-(amidinyl-methyl)phenyl  742 CF₃ 2-F-phenyl 2-(2-imidazolidinyl-methyl)phenyl  743 CF₃ 2-F-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  744 CF₃ 2-F-phenyl 2-dimethylaminoimidazol-1-yl  745 CF₃ 2-F-phenyl 2-(3-aminophenyl)  746 CF₃ 2-F-phenyl 2-(3-pyrrolidinylcarbonyl)  747 CF₃ 2-F-phenyl 2-glycinoyl  748 CF₃ 2-F-phenyl 2-(imidazol-1-ylacetyl)  749 CF₃ 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  750 CF₃ 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl  751 CF₃ 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl  752 CF₃ 2,5-diF-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  753 CF₃ 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl  754 CF₃ 2,5-diF-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  755 CF₃ 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl  756 CF₃ 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl  757 CF₃ 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl  758 CF₃ 2,5-diF-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  759 CF₃ 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl  760 CF₃ 2,5-diF-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  761 CF₃ 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl  762 CF₃ 2,5-diF-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  763 CF₃ 2,5-diF-phenyl 2-(amidinyl)phenyl  764 CF₃ 2,5-diF-phenyl 2-(N-guanidinyl)phenyl  765 CF₃ 2,5-diF-phenyl 2-(imidazolyl)phenyl  766 CF₃ 2,5-diF-phenyl 2-(imidazolidinyl)phenyl  767 CF₃ 2,5-diF-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  768 CF₃ 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl  769 CF₃ 2,5-diF-phenyl 2-(2-piperidinyl)phenyl  770 CF₃ 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl  771 CF₃ 2,5-diF-phenyl 2-(2-imidazolidinyl-methyl)phenyl  772 CF₃ 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  773 CF₃ 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl  774 CF₃ 2,5-diF-phenyl 2-(3-aminophenyl)  775 CF₃ 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl)  776 CF₃ 2,5-diF-phenyl 2-glycinoyl  777 CF₃ 2,5-diF-phenyl 2-(imidazol-1-ylacetyl)  778 CONH₂ phenyl 2-(aminosulfonyl)phenyl  779 CONH₂ phenyl 2-(methylaminosulfonyl)phenyl  780 CONH₂ phenyl 1-pyrrolidinocarbonyl  781 CONH₂ phenyl 2-(methylsulfonyl)phenyl  782 CONH₂ phenyl 4-morpholino  783 CONH₂ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  784 CONH₂ phenyl 4-morpholinocarbonyl  785 CONH₂ 2-pyridyl 2-(aminosulfonyl)phenyl  786 CONH₂ 2-pyridyl 2-(methylaminosulfonyl)phenyl  787 CONH₂ 2-pyridyl 1-pyrrolidinocarbonyl  788 CONH₂ 2-pyridyl 2-(methylsulfonyl)phenyl  789 CONH₂ 2-pyridyl 4-morpholino  790 CONH₂ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  791 CONH₂ 2-pyridyl 4-morpholinocarbonyl  792 CONH₂ 3-pyridyl 2-(aminosulfonyl)phenyl  793 CONH₂ 3-pyridyl 2-(methylaminosulfonyl)phenyl  794 CONH₂ 3-pyridyl 1-pyrrolidinocarbonyl  795 CONH₂ 3-pyridyl 2-(methylsulfonyl)phenyl  796 CONH₂ 3-pyridyl 4-morpholino  797 CONH₂ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  798 CONH₂ 3-pyridyl 4-morpholinocarbonyl  799 CONH₂ 2-pyrimidyl 2-(aminosulfonyl)phenyl  800 CONH₂ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl  801 CONH₂ 2-pyrimidyl 1-pyrrolidinocarbonyl  802 CONH₂ 2-pyrimidyl 2-(methylsulfonyl)phenyl  803 CONH₂ 2-pyrimidyl 4-morpholino  804 CONH₂ 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  805 CONH₂ 2-pyrimidyl 4-morpholinocarbonyl  806 CONH₂ 5-pyrimidyl 2-(aminosulfonyl)phenyl  807 CONH₂ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl  808 CONH₂ 5-pyrimidyl 1-pyrrolidinocarbonyl  809 CONH₂ 5-pyrimidyl 2-(methylsulfonyl)phenyl  810 CONH₂ 5-pyrimidyl 4-morpholino  811 CONH₂ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  812 CONH₂ 5-pyrimidyl 4-morpholinocarbonyl  813 CONH₂ 2-Cl-phenyl 2-(aminosulfonyl)phenyl  814 CONH₂ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl  815 CONH₂ 2-Cl-phenyl 1-pyrrolidinocarbonyl  816 CONH₂ 2-Cl-phenyl 2-(methylsulfonyl)phenyl  817 CONH₂ 2-Cl-phenyl 4-morpholino  818 CONH₂ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  819 CONH₂ 2-Cl-phenyl 4-morpholinocarbonyl  820 CONH₂ 2-F-phenyl 2-(aminosulfonyl)phenyl  821 CONH₂ 2-F-phenyl 2-(methylaminosulfonyl)phenyl  822 CONH₂ 2-F-phenyl 1-pyrrolidinocarbonyl  823 CONH₂ 2-F-phenyl 2-(methylsulfonyl)phenyl  824 CONH₂ 2-F-phenyl 4-morpholino  825 CONH₂ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  826 CONH₂ 2-F-phenyl 4-morpholinocarbonyl  827 CONH₂ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl  828 CONH₂ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl  829 CONH₂ 2,5-diF-phenyl 1-pyrrolidinocarbonyl  830 CONH₂ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl  831 CONH₂ 2,5-diF-phenyl 4-morpholino  832 CONH₂ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  833 CONH₂ 2,5-diF-phenyl 4-morpholinocarbonyl  834 CONH₂ phenyl 2-(N-pyrrolidinyl-methyl)phenyl  835 CONH₂ phenyl 2-(N-piperidinyl-methyl)phenyl  836 CONH₂ phenyl 2-(N-morpholino-methyl)phenyl  837 CONH₂ phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  838 CONH₂ phenyl 2-(N-pyridinium-methyl)phenyl  839 CONH₂ phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  840 CONH₂ phenyl 2-(N-azatanyl-methyl)phenyl  841 CONH₂ phenyl 2-(N-azetidinyl-methyl)phenyl  842 CONH₂ phenyl 2-(N-piperazinyl-methyl)phenyl  843 CONH₂ phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  844 CONH₂ phenyl 2-(N-imidazolyl-methyl)phenyl  845 CONH₂ phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  846 CONH₂ phenyl 2-(N-pyridonyl-methyl)phenyl  847 CONH₂ phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  848 CONH₂ phenyl 2-(amidinyl)phenyl  849 CONH₂ phenyl 2-(N-guanidinyl)phenyl  850 CONH₂ phenyl 2-(imidazolyl)phenyl  851 CONH₂ phenyl 2-(imidazolidinyl)phenyl  852 CONH₂ phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  853 CONH₂ phenyl 2-(2-pyrrolidinyl)phenyl  854 CONH₂ phenyl 2-(2-piperidinyl)phenyl  855 CONH₂ phenyl 2-(amidinyl-methyl)phenyl  856 CONH₂ phenyl 2-(2-imidazolidinyl-methyl)phenyl  857 CONH₂ phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  858 CONH₂ phenyl 2-dimethylaminoimidazol-1-yl  859 CONH₂ phenyl 2-(3-aminophenyl)  860 CONH₂ phenyl 2-(3-pyrrolidinylcarbonyl)  861 CONH₂ phenyl 2-glycinoyl  862 CONH₂ phenyl 2-(imidazol-1-ylacetyl)  863 CONH₂ 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl  864 CONH₂ 2-pyridyl 2-(N-piperidinyl-methyl)phenyl  865 CONH₂ 2-pyridyl 2-(N-morpholino-methyl)phenyl  866 CONH₂ 2-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl  867 CONH₂ 2-pyridyl 2-(N-pyridinium-methyl)phenyl  868 CONH₂ 2-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  869 CONH₂ 2-pyridyl 2-(N-azatanyl-methyl)phenyl  870 CONH₂ 2-pyridyl 2-(N-azetidinyl-methyl)phenyl  871 CONH₂ 2-pyridyl 2-(N-piperazinyl-methyl)phenyl  872 CONH₂ 2-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  873 CONH₂ 2-pyridyl 2-(N-imidazolyl-methyl)phenyl  874 CONH₂ 2-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl  875 CONH₂ 2-pyridyl 2-(N-pyridonyl-methyl)phenyl  876 CONH₂ 2-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  877 CONH₂ 2-pyridyl 2-(amidinyl)phenyl  878 CONH₂ 2-pyridyl 2-(N-guanidinyl)phenyl  879 CONH₂ 2-pyridyl 2-(imidazolyl)phenyl  880 CONH₂ 2-pyridyl 2-(imidazolidinyl)phenyl  881 CONH₂ 2-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl  882 CONH₂ 2-pyridyl 2-(2-pyrrolidinyl)phenyl  883 CONH₂ 2-pyridyl 2-(2-piperidinyl)phenyl  884 CONH₂ 2-pyridyl 2-(amidinyl-methyl)phenyl  885 CONH₂ 2-pyridyl 2-(2-imidazolidinyl-methyl)phenyl  886 CONH₂ 2-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  887 CONH₂ 2-pyridyl 2-dimethylaminoimidazol-1-yl  888 CONH₂ 2-pyridyl 2-(3-aminophenyl)  889 CONH₂ 2-pyridyl 2-(3-pyrrolidinylcarbonyl)  890 CONH₂ 2-pyridyl 2-glycinoyl  891 CONH₂ 2-pyridyl 2-(imidazol-1-ylacetyl)  892 CONH₂ 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl  893 CONH₂ 3-pyridyl 2-(N-piperidinyl-methyl)phenyl  894 CONH₂ 3-pyridyl 2-(N-morpholino-methyl)phenyl  895 CONH₂ 3-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl  896 CONH₂ 3-pyridyl 2-(N-pyridinium-methyl)phenyl  897 CONH₂ 3-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  898 CONH₂ 3-pyridyl 2-(N-azatanyl-methyl)phenyl  899 CONH₂ 3-pyridyl 2-(N-azetidinyl-methyl)phenyl  900 CONH₂ 3-pyridyl 2-(N-piperazinyl-methyl)phenyl  901 CONH₂ 3-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  902 CONH₂ 3-pyridyl 2-(N-imidazolyl-methyl)phenyl  903 CONH₂ 3-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl  904 CONH₂ 3-pyridyl 2-(N-pyridonyl-methyl)phenyl  905 CONH₂ 3-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  906 CONH₂ 3-pyridyl 2-(amidinyl)phenyl  907 CONH₂ 3-pyridyl 2-(N-guanidinyl)phenyl  908 CONH₂ 3-pyridyl 2-(imidazolyl)phenyl  909 CONH₂ 3-pyridyl 2-(imidazolidinyl)phenyl  910 CONH₂ 3-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl  911 CONH₂ 3-pyridyl 2-(2-pyrrolidinyl)phenyl  912 CONH₂ 3-pyridyl 2-(2-piperidinyl)phenyl  913 CONH₂ 3-pyridyl 2-(amidinyl-methyl)phenyl  914 CONH₂ 3-pyridyl 2-(2-imidazolidinyl-methyl)phenyl  915 CONH₂ 3-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  916 CONH₂ 3-pyridyl 2-dimethylaminoimidazol-1-yl  917 CONH₂ 3-pyridyl 2-(3-aminophenyl)  918 CONH₂ 3-pyridyl 2-(3-pyrrolidinylcarbonyl)  919 CONH₂ 3-pyridyl 2-glycinoyl  920 CONH₂ 3-pyridyl 2-(imidazol-1-ylacetyl)  921 CONH₂ 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl  922 CONH₂ 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl  923 CONH₂ 2-pyrimidyl 2-(N-morpholino-methyl)phenyl  924 CONH₂ 2-pyrimidyl 2-(N,N′-methylmorpholinium-methyl)phenyl  925 CONH₂ 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl  926 CONH₂ 2-pyrimidyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  927 CONH₂ 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl  928 CONH₂ 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl  929 CONH₂ 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl  930 CONH₂ 2-pyrimidyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  931 CONH₂ 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl  932 CONH₂ 2-pyrimidyl 2-(N-methoxy-N-methylamino-methyl)phenyl  933 CONH₂ 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl  934 CONH₂ 2-pyrimidyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  935 CONH₂ 2-pyrimidyl 2-(amidinyl)phenyl  936 CONH₂ 2-pyrimidyl 2-(N-guanidinyl)phenyl  937 CONH₂ 2-pyrimidyl 2-(imidazolyl)phenyl  938 CONH₂ 2-pyrimidyl 2-(imidazolidinyl)phenyl  939 CONH₂ 2-pyrimidyl 2-(2-imidazolidinyl-sulfonyl)phenyl  940 CONH₂ 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl  941 CONH₂ 2-pyrimidyl 2-(2-piperidinyl)phenyl  942 CONH₂ 2-pyrimidyl 2-(amidinyl-methyl)phenyl  943 CONH₂ 2-pyrimidyl 2-(2-imidazolidinyl-methyl)phenyl  944 CONH₂ 2-pyrimidyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  945 CONH₂ 2-pyrimidyl 2-dimethylaminoimidazol-1-yl  946 CONH₂ 2-pyrimidyl 2-(3-aminophenyl)  947 CONH₂ 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl)  948 CONH₂ 2-pyrimidyl 2-glycinoyl  949 CONH₂ 2-pyrimidyl 2-(imidazol-1-ylacetyl)  950 CONH₂ 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  951 CONH₂ 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl  952 CONH₂ 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl  953 CONH₂ 2-Cl-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  954 CONH₂ 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl  955 CONH₂ 2-Cl-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  956 CONH₂ 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl  957 CONH₂ 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl  958 CONH₂ 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl  959 CONH₂ 2-Cl-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  960 CONH₂ 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl  961 CONH₂ 2-Cl-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  962 CONH₂ 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl  963 CONH₂ 2-Cl-phenyl 2-(N-(N′,N-dimethylhydrazinyl-methyl)phenyl  964 CONH₂ 2-Cl-phenyl 2-(amidinyl)phenyl  965 CONH₂ 2-Cl-phenyl 2-(N-guanidinyl)phenyl  966 CONH₂ 2-Cl-phenyl 2-(imidazolyl)phenyl  967 CONH₂ 2-Cl-phenyl 2-(imidazolidinyl)phenyl  968 CONH₂ 2-Cl-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  969 CONH₂ 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl  970 CONH₂ 2-Cl-phenyl 2-(2-piperidinyl)phenyl  971 CONH₂ 2-Cl-phenyl 2-(amidinyl-methyl)phenyl  972 CONH₂ 2-Cl-phenyl 2-(2-imidazolidinyl-methyl)phenyl  973 CONH₂ 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl  974 CONH₂ 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl  975 CONH₂ 2-Cl-phenyl 2-(3-aminophenyl)  976 CONH₂ 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl)  977 CONH₂ 2-Cl-phenyl 2-glycinoyl  978 CONH₂ 2-Cl-phenyl 2-(imidazol-1-ylacetyl)  979 CONH₂ 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl  980 CONH₂ 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl  981 CONH₂ 2-F-phenyl 2-(N-morpholino-methyl)phenyl  982 CONH₂ 2-F-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl  983 CONH₂ 2-F-phenyl 2-(N-pyridinium-methyl)phenyl  984 CONH₂ 2-F-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl  985 CONH₂ 2-F-phenyl 2-(N-azatanyl-methyl)phenyl  986 CONH₂ 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl  987 CONH₂ 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl  988 CONH₂ 2-F-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl  989 CONH₂ 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl  990 CONH₂ 2-F-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl  991 CONH₂ 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl  992 CONH₂ 2-F-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl  993 CONH₂ 2-F-phenyl 2-(amidinyl)phenyl  994 CONH₂ 2-F-phenyl 2-(N-guanidinyl)phenyl  995 CONH₂ 2-F-phenyl 2-(imidazolyl)phenyl  996 CONH₂ 2-F-phenyl 2-(imidazolidinyl)phenyl  997 CONH₂ 2-F-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl  998 CONH₂ 2-F-phenyl 2-(2-pyrrolidinyl)phenyl  999 CONH₂ 2-F-phenyl 2-(2-piperidinyl)phenyl 1000 CONH₂ 2-F-phenyl 2-(amidinyl-methyl)phenyl 1001 CONH₂ 2-F-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1002 CONH₂ 2-F-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1003 CONH₂ 2-F-phenyl 2-dimethylaminoimidazol-1-yl 1004 CONH₂ 2-F-phenyl 2-(3-aminophenyl) 1005 CONH₂ 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 1006 CONH₂ 2-F-phenyl 2-glycinoyl 1007 CONH₂ 2-F-phenyl 2-(imidazol-1-ylacetyl) 1008 CONH₂ 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1009 CONH₂ 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 1010 CONH₂ 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 1011 CONH₂ 2,5-diF-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1012 CONH₂ 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 1013 CONH₂ 2,5-diF-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1014 CONH₂ 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 1015 CONH₂ 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 1016 CONH₂ 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 1017 CONH₂ 2,5-diF-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1018 CONH₂ 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 1019 CONH₂ 2,5-diF-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1020 CONH₂ 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 1021 CONH₂ 2,5-diF-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1022 CONH₂ 2,5-diF-phenyl 2-(amidinyl)phenyl 1023 CONH₂ 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 1024 CONH₂ 2,5-diF-phenyl 2-(imidazolyl)phenyl 1025 CONH₂ 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 1026 CONH₂ 2,5-diF-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1027 CONH₂ 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 1028 CONH₂ 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 1029 CONH₂ 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 1030 CONH₂ 2,5-diF-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1031 CONH₂ 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1032 CONH₂ 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 1033 CONH₂ 2,5-diF-phenyl 2-(3-aminophenyl) 1034 CONH₂ 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 1035 CONH₂ 2,5-diF-phenyl 2-glycinoyl 1036 CONH₂ 2,5-diF-phenyl 2-(imidazol-1-ylacetyl) 1037 SCH₃ phenyl 2-(aminosulfonyl)phenyl 1038 SCH₃ phenyl 2-(methylaminosulfonyl)phenyl 1039 SCH₃ phenyl 1-pyrrolidinocarbonyl 1040 SCH₃ phenyl 2-(methylsulfonyl)phenyl 1041 SCH₃ phenyl 4-morpholino 1042 SCH₃ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1043 SCH₃ phenyl 4-morpholinocarbonyl 1044 SCH₃ 2-pyridyl 2-(aminosulfonyl)phenyl 1045 SCH₃ 2-pyridyl 2-(methylaminosulfonyl)phenyl 1046 SCH₃ 2-pyridyl 1-pyrrolidinocarbonyl 1047 SCH₃ 2-pyridyl 2-(methylsulfonyl)phenyl 1048 SCH₃ 2-pyridyl 4-morpholino 1049 SCH₃ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1050 SCH₃ 2-pyridyl 4-morpholinocarbonyl 1051 SCH₃ 3-pyridyl 2-(aminosulfonyl)phenyl 1052 SCH₃ 3-pyridyl 2-(methylaminosulfonyl)phenyl 1053 SCH₃ 3-pyridyl 1-pyrrolidinocarbonyl 1054 SCH₃ 3-pyridyl 2-(methylsulfonyl)phenyl 1055 SCH₃ 3-pyridyl 4-morpholino 1056 SCH₃ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1057 SCH₃ 3-pyridyl 4-morpholinocarbonyl 1058 SCH₃ 2-pyrimidyl 2-(aminosulfonyl)phenyl 1059 SCH₃ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 1060 SCH₃ 2-pyrimidyl 1-pyrrolidinocarbonyl 1061 SCH₃ 2-pyrimidyl 2-(methylsulfonyl)phenyl 1062 SCH₃ 2-pyrimidyl 4-morpholino 1063 SCH₃ 2-pyrimidyl 2 (1′-CF₃-tetrazol-2-yl)phenyl 1064 SCH₃ 2-pyrimidyl 4-morpholinocarbonyl 1065 SCH₃ 5-pyrimidyl 2-(aminosulfonyl)phenyl 1066 SCH₃ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 1067 SCH₃ 5-pyrimidyl 1-pyrrolidinocarbonyl 1068 SCH₃ 5-pyrimidyl 2-(methylsulfonyl)phenyl 1069 SCH₃ 5-pyrimidyl 4-morpholino 1070 SCH₃ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1071 SCH₃ 5-pyrimidyl 4-morpholinocarbonyl 1072 SCH₃ 2-Cl-phenyl 2-(aminosulfonyl)phenyl 1073 SCH₃ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 1074 SCH₃ 2-Cl-phenyl 1-pyrrolidinocarbonyl 1075 SCH₃ 2-Cl-phenyl 2-(methylsulfonyl)phenyl 1076 SCH₃ 2-Cl-phenyl 4-morpholino 1077 SCH₃ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1078 SCH₃ 2-Cl-phenyl 4-morpholinocarbonyl 1079 SCH₃ 2-F-phenyl 2-(aminosulfonyl)phenyl 1080 SCH₃ 2-F-phenyl 2-(methylaminosulfonyl)phenyl 1081 SCH₃ 2-F-phenyl 1-pyrrolidinocarbonyl 1082 SCH₃ 2-F-phenyl 2-(methylsulfonyl)phenyl 1083 SCH₃ 2-F-phenyl 4-morpholino 1084 SCH₃ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1085 SCH₃ 2-F-phenyl 4-morpholinocarbonyl 1086 SCH₃ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 1087 SCH₃ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 1088 SCH₃ 2,5-diF-phenyl 1-pyrrolidinocarbonyl 1089 SCH₃ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 1090 SCH₃ 2,5-diF-phenyl 4-morpholino 1091 SCH₃ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1092 SCH₃ 2,5-diF-phenyl 4-morpholinocarbonyl 1093 SCH₃ phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1094 SCH₃ phenyl 2-(N-piperidinyl-methyl)phenyl 1095 SCH₃ phenyl 2-(N-morpholino-methyl)phenyl 1096 SCH₃ phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1097 SCH₃ phenyl 2-(N-pyridinium-methyl)phenyl 1098 SCH₃ phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1099 SCH₃ phenyl 2-(N-azatanyl-methyl)phenyl 1100 SCH₃ phenyl 2-(N-azetidinyl-methyl)phenyl 1101 SCH₃ phenyl 2-(N-piperazinyl-methyl)phenyl 1102 SCH₃ phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1103 SCH₃ phenyl 2-(N-imidazolyl-methyl)phenyl 1104 SCH₃ phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1105 SCH₃ phenyl 2-(N-pyridonyl-methyl)phenyl 1106 SCH₃ phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1107 SCH₃ phenyl 2-(amidinyl)phenyl 1108 SCH₃ phenyl 2-(N-guanidinyl)phenyl 1109 SCH₃ phenyl 2-(imidazolyl)phenyl 1110 SCH₃ phenyl 2-(imidazolidinyl)phenyl 1111 SCH₃ phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1112 SCH₃ phenyl 2-(2-pyrrolidinyl)phenyl 1113 SCH₃ phenyl 2-(2-piperidinyl)phenyl 1114 SCH₃ phenyl 2-(amidinyl-methyl)phenyl 1115 SCH₃ phenyl 2-(2-imidazolidinyl-methyl)phenyl 1116 SCH₃ phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1117 SCH₃ phenyl 2-dimethylaminoimidazol-1-yl 1118 SCH₃ phenyl 2-(3-aminophenyl) 1119 SCH₃ phenyl 2-(3-pyrrolidinylcarbonyl) 1120 SCH₃ phenyl 2-glycinoyl 1121 SCH₃ phenyl 2-(imidazol-1-ylacetyl) 1122 SCH₃ 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1123 SCH₃ 2-pyridyl 2-(N-piperidinyl-methyl)phenyl 1124 SCH₃ 2-pyridyl 2-(N-morpholino-methyl)phenyl 1125 SCH₃ 2-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1126 SCH₃ 2-pyridyl 2-(N-pyridinium-methyl)phenyl 1127 SCH₃ 2-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1128 SCH₃ 2-pyridyl 2-(N-azatanyl-methyl)phenyl 1129 SCH₃ 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 1130 SCH₃ 2-pyridyl 2-(N-piperazinyl-methyl)phenyl 1131 SCH₃ 2-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1132 SCH₃ 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 1133 SCH₃ 2-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1134 SCH₃ 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 1135 SCH₃ 2-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1136 SCH₃ 2-pyridyl 2-(amidinyl)phenyl 1137 SCH₃ 2-pyridyl 2-(N-guanidinyl)phenyl 1138 SCH₃ 2-pyridyl 2-(imidazolyl)phenyl 1139 SCH₃ 2-pyridyl 2-(imidazolidinyl)phenyl 1140 SCH₃ 2-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1141 SCH₃ 2-pyridyl 2-(2-pyrrolidinyl)phenyl 1142 SCH₃ 2-pyridyl 2-(2-piperidinyl)phenyl 1143 SCH₃ 2-pyridyl 2-(amidinyl-methyl)phenyl 1144 SCH₃ 2-pyridyl 2-(2-imidazolidinyl-methyl)phenyl 1145 SCH₃ 2-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1146 SCH₃ 2-pyridyl 2-dimethylaminoimidazol-1-yl 1147 SCH₃ 2-pyridyl 2-(3-aminophenyl) 1148 SCH₃ 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 1149 SCH₃ 2-pyridyl 2-glycinoyl 1150 SCH₃ 2-pyridyl 2-(imidazol-1-ylacetyl) 1151 SCH₃ 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1152 SCH₃ 3-pyridyl 2-(N-piperidinyl-methyl)phenyl 1153 SCH₃ 3-pyridyl 2-(N-morpholino-methyl)phenyl 1154 SCH₃ 3-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1155 SCH₃ 3-pyridyl 2-(N-pyridinium-methyl)phenyl 1156 SCH₃ 3-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1157 SCH₃ 3-pyridyl 2-(N-azatanyl-methyl)phenyl 1158 SCH₃ 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 1159 SCH₃ 3-pyridyl 2-(N-piperazinyl-methyl)phenyl 1160 SCH₃ 3-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1161 SCH₃ 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 1162 SCH₃ 3-pyridel 2-(N-methoxy-N-methylamino-methyl)phenyl 1163 SCH₃ 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 1164 SCH₃ 3-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1165 SCH₃ 3-pyridyl 2-(amidinyl)phenyl 1166 SCH₃ 3-pyridyl 2-(N-guanidinyl)phenyl 1167 SCH₃ 3-pyridyl 2-(imidazolyl)phenyl 1168 SCH₃ 3-pyridyl 2-(imidazolidinyl)phenyl 1169 SCH₃ 3-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1170 SCH₃ 3-pyridyl 2-(2-pyrrolidinyl)phenyl 1171 SCH₃ 3-pyridyl 2-(2-piperidinyl)phenyl 1172 SCH₃ 3-pyridyl 2-(amidinyl-methyl)phenyl 1173 SCH₃ 3-pyridyl 2-(2-imidazolidinyl-methyl)phenyl 1174 SCH₃ 3-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1175 SCH₃ 3-pyridyl 2-dimethylaminoimidazol-1-yl 1176 SCH₃ 3-pyridyl 2-(3-aminophenyl) 1177 SCH₃ 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 1178 SCH₃ 3-pyridyl 2-glycinoyl 1179 SCH₃ 3-pyridyl 2-(imidazol-1-ylacetyl) 1180 SCH₃ 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 1181 SCH₃ 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl 1182 SCH₃ 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 1183 SCH₃ 2-pyrimidyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1184 SCH₃ 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 1185 SCH₃ 2-pyrimidyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1186 SCH₃ 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 1187 SCH₃ 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl 1188 SCH₃ 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl 1189 SCH₃ 2-pyrimidyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1190 SCH₃ 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 1191 SCH₃ 2-pyrimidyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1192 SCH₃ 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 1193 SCH₃ 2-pyrimidyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1194 SCH₃ 2-pyrimidyl 2-(amidinyl)phenyl 1195 SCH₃ 2-pyrimidyl 2-(N-guanidinyl)phenyl 1196 SCH₃ 2-pyrimidyl 2-(imidazolyl)phenyl 1197 SCH₃ 2-pyrimidyl 2-(imidazolidinyl)phenyl 1198 SCH₃ 2-pyrimidyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1199 SCH₃ 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl 1200 SCH₃ 2-pyrimidyl 2-(2-piperidinyl)phenyl 1201 SCH₃ 2-pyrimidyl 2-(amidinyl-methyl)phenyl 1202 SCH₃ 2-pyrimidyl 2-(2-imidazolidinyl-methyl)phenyl 1203 SCH₃ 2-pyrimidyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1204 SCH₃ 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 1205 SCH₃ 2-pyrimidyl 2-(3-aminophenyl) 1206 SCH₃ 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 1207 SCH₃ 2-pyrimidyl 2-glycinoyl 1208 SCH₃ 2-pyrimidyl 2-(imidazol-1-ylacetyl) 1209 SCH₃ 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1210 SCH₃ 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl 1211 SCH₃ 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 1212 SCH₃ 2-Cl-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1213 SCH₃ 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 1214 SCH₃ 2-Cl-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1215 SCH₃ 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 1216 SCH₃ 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl 1217 SCH₃ 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl 1218 SCH₃ 2-Cl-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1219 SCH₃ 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 1220 SCH₃ 2-Cl-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1221 SCH₃ 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 1222 SCH₃ 2-Cl-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1223 SCH₃ 2-Cl-phenyl 2-(amidinyl)phenyl 1224 SCH₃ 2-Cl-phenyl 2-(N-guanidinyl)phenyl 1225 SCH₃ 2-Cl-phenyl 2-(imidazolyl)phenyl 1226 SCH₃ 2-Cl-phenyl 2-(imidazolidinyl)phenyl 1227 SCH₃ 2-Cl-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1228 SCH₃ 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 1229 SCH₃ 2-Cl-phenyl 2-(2-piperidinyl)phenyl 1230 SCH₃ 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 1231 SCH₃ 2-Cl-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1232 SCH₃ 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1233 SCH₃ 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 1234 SCH₃ 2-Cl-phenyl 2-(3-aminophenyl) 1235 SCH₃ 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 1236 SCH₃ 2-Cl-phenyl 2-glycinoyl 1237 SCH₃ 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 1238 SCH₃ 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1239 SCH₃ 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl 1240 SCH₃ 2-F-phenyl 2-(N-morpholino-methyl)phenyl 1241 SCH₃ 2-F-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1242 SCH₃ 2-F-phenyl 2-(N-pyridinium-methyl)phenyl 1243 SCH₃ 2-F-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1244 SCH₃ 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 1245 SCH₃ 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl 1246 SCH₃ 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl 1247 SCH₃ 2-F-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1248 SCH₃ 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 1249 SCH₃ 2-F-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1250 SCH₃ 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 1251 SCH₃ 2-F-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1252 SCH₃ 2-F-phenyl 2-(amidinyl)phenyl 1253 SCH₃ 2-F-phenyl 2-(N-guanidinyl)phenyl 1254 SCH₃ 2-F-phenyl 2-(imidazolyl)phenyl 1255 SCH₃ 2-F-phenyl 2-(imidazolidinyl)phenyl 1256 SCH₃ 2-F-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1257 SCH₃ 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 1258 SCH₃ 2-F-phenyl 2-(2-piperidinyl)phenyl 1259 SCH₃ 2-F-phenyl 2-(amidinyl-methyl)phenyl 1260 SCH₃ 2-F-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1261 SCH₃ 2-F-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1262 SCH₃ 2-F-phenyl 2-dimethylaminoimidazol-1-yl 1263 SCH₃ 2-F-phenyl 2-(3-aminophenyl) 1264 SCH₃ 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 1265 SCH₃ 2-F-phenyl 2-glycinoyl 1266 SCH₃ 2-F-phenyl 2-(imidazol-1-ylacetyl) 1267 SCH₃ 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1268 SCH₃ 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 1269 SCH₃ 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 1270 SCH₃ 2,5-diF-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1271 SCH₃ 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 1272 SCH₃ 2,5-diF-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1273 SCH₃ 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 1274 SCH₃ 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 1275 SCH₃ 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 1276 SCH₃ 2,5-diF-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1277 SCH₃ 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 1278 SCH₃ 2,5-diF-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1279 SCH₃ 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 1280 SCH₃ 2,5-diF-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1281 SCH₃ 2,5-diF-phenyl 2-(amidinyl)phenyl 1282 SCH₃ 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 1283 SCH₃ 2,5-diF-phenyl 2-(imidazolyl)phenyl 1284 SCH₃ 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 1285 SCH₃ 2,5-diF-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1286 SCH₃ 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 1287 SCH₃ 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 1288 SCH₃ 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 1289 SCH₃ 2,5-diF-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1290 SCH₃ 2,5-diF-phenyl 2-(N-(2-aminolinidazolyl)-methyl)phenyl 1291 SCH₃ 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 1292 SCH₃ 2,5-diF-phenyl 2-(3-aminophenyl) 1293 SCH₃ 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 1294 SCH₃ 2,5-diF-phenyl 2-glycinoyl 1295 SCH₃ 2,5-diF-phenyl 2-(imidazol-1-ylacetyl) 1296 SO₂CH₃ phenyl 2-(aminosulfonyl)phenyl 1297 SO₂CH₃ phenyl 2-(methylaminosulfonyl)phenyl 1298 SO₂CH₃ phenyl 1-pyrrolidinocarbonyl 1299 SO₂CH₃ phenyl 2-(methylsulfonyl)phenyl 1300 SO₂CH₃ phenyl 4-morpholino 1301 SO₂CH₃ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1302 SO₂CH₃ phenyl 4-morpholinocarbonyl 1303 SO₂CH₃ 2-pyridyl 2-(aminosulfonyl)phenyl 1304 SO₂CH₃ 2-pyridyl 2-(methylaminosulfonyl)phenyl 1305 SO₂CH₃ 2-pyridyl 1-pyrrolidinocarbonyl 1306 SO₂CH₃ 2-pyridyl 2-(methylsulfonyl)phenyl 1307 SO₂CH₃ 2-pyridyl 4-morpholino 1308 SO₂CH₃ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1309 SO₂CH₃ 2-pyridyl 4-morpholinocarbonyl 1310 SO₂CH₃ 3-pyridyl 2-(aminosulfonyl)phenyl 1311 SO₂CH₃ 3-pyridyl 2-(methylaminosulfonyl)phenyl 1312 SO₂CH₃ 3-pyridyl 1-pyrrolidinocarbonyl 1313 SO₂CH₃ 3-pyridyl 2-(methylsulfonyl)phenyl 1314 SO₂CH₃ 3-pyridyl 4-morpholino 1315 SO₂CH₃ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1316 SO₂CH₃ 3-pyridyl 4-morpholinocarbonyl 1317 SO₂CH₃ 2-pyrimidyl 2-(aminosulfonyl)phenyl 1318 SO₂CH₃ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 1319 SO₂CH₃ 2-pyrimidyl 1-pyrrolidinocarbonyl 1320 SO₂CH₃ 2-pyrimidyl 2-(methylsulfonyl)phenyl 1321 SO₂CH₃ 2-pyrimidyl 4-morpholino 1322 SO₂CH₃ 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1323 SO₂CH₃ 2-pyrimidyl 4-morpholinocarbonyl 1324 SO₂CH₃ 5-pyrimidyl 2-(aminosulfonyl)phenyl 1325 SO₂CH₃ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 1326 SO₂CH₃ 5-pyrimidyl 1-pyrrolidinocarbonyl 1327 SO₂CH₃ 5-pyrimidyl 2-(methylsulfonyl)phenyl 1328 SO₂CH₃ 5-pyrimidyl 4-morpholino 1329 SO₂CH₃ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1330 SO₂CH₃ 5-pyrimidyl 4-morpholinocarbonyl 1331 SO₂CH₃ 2-Cl-phenyl 2-(aminosulfonyl)phenyl 1332 SO₂CH₃ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 1333 SO₂CH₃ 2-Cl-phenyl 1-pyrrolidinocarbonyl 1334 SO₂CH₃ 2-Cl-phenyl 2-(methylsulfonyl)phenyl 1335 SO₂CH₃ 2-Cl-phenyl 4-morpholino 1336 SO₂CH₃ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1337 SO₂CH₃ 2-Cl-phenyl 4-morpholinocarbonyl 1338 SO₂CH₃ 2-F-phenyl 2-(aminosulfonyl)phenyl 1339 SO₂CH₃ 2-F-phenyl 2-(methylaminosulfonyl)phenyl 1340 SO₂CH₃ 2-F-phenyl 1-pyrrolidinocarbonyl 1341 SO₂CH₃ 2-F-phenyl 2-(methylsulfonyl)phenyl 1342 SO₂CH₃ 2-F-phenyl 4-morpholino 1343 SO₂CH₃ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1344 SO₂CH₃ 2-F-phenyl 4-morpholinocarbonyl 1345 SO₂CH₃ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 1346 SO₂CH₃ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 1347 SO₂CH₃ 2,5-diF-phenyl 1-pyrrolidinocarbonyl 1348 SO₂CH₃ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 1349 SO₂CH₃ 2,5-diF-phenyl 4-morpholino 1350 SO₂CH₃ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1351 SO₂CH₃ 2,5-diF-phenyl 4-morpholinocarbonyl 1352 SO₂CH₃ phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1353 SO₂CH₃ phenyl 2-(N-piperidinyl-methyl)phenyl 1354 SO₂CH₃ phenyl 2-(N-morpholino-methyl)phenyl 1355 SO₂CH₃ phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1356 SO₂CH₃ phenyl 2-(N-pyridinium-methyl)phenyl 1357 SO₂CH₃ phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1358 SO₂CH₃ phenyl 2-(N-azatanyl-methyl)phenyl 1359 SO₂CH₃ phenyl 2-(N-azetidinyl-methyl)phenyl 1360 SO₂CH₃ phenyl 2-(N-piperazinyl-methyl)phenyl 1361 SO₂CH₃ phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1362 SO₂CH₃ phenyl 2-(N-imidazolyl-methyl)phenyl 1363 SO₂CH₃ phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1364 SO₂CH₃ phenyl 2-(N-pyridonyl-methyl)phenyl 1365 SO₂CH₃ phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1366 SO₂CH₃ phenyl 2-(amidinyl)phenyl 1367 SO₂CH₃ phenyl 2-(N-guanidinyl)phenyl 1368 SO₂CH₃ phenyl 2-(imidazolyl)phenyl 1369 SO₂CH₃ phenyl 2-(imidazolidinyl)phenyl 1370 SO₂CH₃ phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1371 SO₂CH₃ phenyl 2-(2-pyrrolidinyl)phenyl 1372 SO₂CH₃ phenyl 2-(2-piperidinyl)phenyl 1373 SO₂CH₃ phenyl 2-(amidinyl-methyl)phenyl 1374 SO₂CH₃ phenyl 2-(2-imidazolidinyl-methyl)phenyl 1375 SO₂CH₃ phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1376 SO₂CH₃ phenyl 2-dimethylaminoimidazol-1-yl 1377 SO₂CH₃ phenyl 2-(3-aminophenyl) 1378 SO₂CH₃ phenyl 2-(3-pyrrolidinylcarbonyl) 1379 SO₂CH₃ phenyl 2-glycinoyl 1380 SO₂CH₃ phenyl 2-(imidazol-1-ylacetyl) 1381 SO₂CH₃ 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1382 SO₂CH₃ 2-pyridyl 2-(N-piperidinyl-methyl)phenyl 1383 SO₂CH₃ 2-pyridyl 2-(N-morpholino-methyl)phenyl 1384 SO₂CH₃ 2-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1385 SO₂CH₃ 2-pyridyl 2-(N-pyridinium-methyl)phenyl 1386 SO₂CH₃ 2-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1387 SO₂CH₃ 2-pyridyl 2-(N-azatanyl-methyl)phenyl 1388 SO₂CH₃ 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 1389 SO₂CH₃ 2-pyridyl 2-(N-piperazinyl-methyl)phenyl 1390 SO₂CH₃ 2-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1391 SO₂CH₃ 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 1392 SO₂CH₃ 2-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1393 SO₂CH₃ 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 1394 SO₂CH₃ 2-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1395 SO₂CH₃ 2-pyridyl 2-(amidinyl)phenyl 1396 SO₂CH₃ 2-pyridyl 2-(N-guanidinyl)phenyl 1397 SO₂CH₃ 2-pyridyl 2-(imidazolyl)phenyl 1398 SO₂CH₃ 2-pyridyl 2-(imidazolidinyl)phenyl 1399 SO₂CH₃ 2-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1400 SO₂CH₃ 2-pyridyl 2-(2-pyrrolidinyl)phenyl 1401 SO₂CH₃ 2-pyridyl 2-(2-piperidinyl)phenyl 1402 SO₂CH₃ 2-pyridyl 2-(amidinyl-methyl)phenyl 1403 SO₂CH₃ 2-pyridyl 2-(2-imidazolidinyl-methyl)phenyl 1404 SO₂CH₃ 2-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1405 SO₂CH₃ 2-pyridyl 2-dimethylaminoimidazol-1-yl 1406 SO₂CH₃ 2-pyridyl 2-(3-aminophenyl) 1407 SO₂CH₃ 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 1408 SO₂CH₃ 2-pyridyl 2-glycinoyl 1409 SO₂CH₃ 2-pyridyl 2-(imidazol-1-ylacetyl) 1410 SO₂CH₃ 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1411 SO₂CH₃ 3-pyridyl 2-(N-piperidinyl-methyl)phenyl 1412 SO₂CH₃ 3-pyridyl 2-(N-morpholino-methyl)phenyl 1413 SO₂CH₃ 3-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1414 SO₂CH₃ 3-pyridyl 2-(N-pyridinium-methyl)phenyl 1415 SO₂CH₃ 3-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1416 SO₂CH₃ 3-pyridyl 2-(N-azatanyl-methyl)phenyl 1417 SO₂CH₃ 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 1418 SO₂CH₃ 3-pyridyl 2-(N-piperazinyl-methyl)phenyl 1419 SO₂CH₃ 3-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1420 SO₂CH₃ 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 1421 SO₂CH₃ 3-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1422 SO₂CH₃ 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 1423 SO₂CH₃ 3-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1424 SO₂CH₃ 3-pyridyl 2-(amidinyl)phenyl 1425 SO₂CH₃ 3-pyridyl 2-(N-guanidinyl)phenyl 1426 SO₂CH₃ 3-pyridyl 2-(imidazolyl)phenyl 1427 SO₂CH₃ 3-pyridyl 2-(imidazolidinyl)phenyl 1428 SO₂CH₃ 3-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1429 SO₂CH₃ 3-pyridyl 2-(2-pyrrolidinyl)phenyl 1430 SO₂CH₃ 3-pyridyl 2-(2-piperidinyl)phenyl 1431 SO₂CH₃ 3-pyridyl 2-(amidinyl-methyl)phenyl 1432 SO₂CH₃ 3-pyridyl 2-(2-imidazolidinyl-methyl)phenyl 1433 SO₂CH₃ 3-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1434 SO₂CH₃ 3-pyridyl 2-dimethylaminoimidazol-1-yl 1435 SO₂CH₃ 3-pyridyl 2-(3-aminophenyl) 1436 SO₂CH₃ 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 1437 SO₂CH₃ 3-pyridyl 2-glycinoyl 1438 SO₂CH₃ 3-pyridyl 2-(imidazol-1-ylacetyl) 1439 SO₂CH₃ 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 1440 SO₂CH₃ 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl 1441 SO₂CH₃ 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 1442 SO₂CH₃ 2-pyrimidyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1443 SO₂CH₃ 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 1444 SO₂CH₃ 2-pyrimidyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1445 SO₂CH₃ 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 1446 SO₂CH₃ 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl 1447 SO₂CH₃ 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl 1448 SO₂CH₃ 2-pyrimidyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1449 SO₂CH₃ 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 1450 SO₂CH₃ 2-pyrimidyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1451 SO₂CH₃ 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 1452 SO₂CH₃ 2-pyrimidyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1453 SO₂CH₃ 2-pyrimidyl 2-(amidinyl)phenyl 1454 SO₂CH₃ 2-pyrimidyl 2-(N-guanidinyl)phenyl 1455 SO₂CH₃ 2-pyrimidyl 2-(imidazolyl)phenyl 1456 SO₂CH₃ 2-pyrimidyl 2-(imidazolidinyl)phenyl 1457 SO₂CH₃ 2-pyrimidyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1458 SO₂CH₃ 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl 1459 SO₂CH₃ 2-pyrimidyl 2-(2-piperidinyl)phenyl 1460 SO₂CH₃ 2-pyrimidyl 2-(amidinyl-methyl)phenyl 1461 SO₂CH₃ 2-pyrimidyl 2-(2-imidazolidinyl-methyl)phenyl 1462 SO₂CH₃ 2-pyrimidyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1463 SO₂CH₃ 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 1464 SO₂CH₃ 2-pyrimidyl 2-(3-aminophenyl) 1465 SO₂CH₃ 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 1466 SO₂CH₃ 2-pyrimidyl 2-glycinoyl 1467 SO₂CH₃ 2-pyrimidyl 2-(imidazol-1-ylacetyl) 1468 SO₂CH₃ 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1469 SO₂CH₃ 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl 1470 SO₂CH₃ 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 1471 SO₂CH₃ 2-Cl-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1472 SO₂CH₃ 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 1473 SO₂CH₃ 2-Cl-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1474 SO₂CH₃ 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 1475 SO₂CH₃ 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl 1476 SO₂CH₃ 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl 1477 SO₂CH₃ 2-Cl-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1478 SO₂CH₃ 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 1479 SO₂CH₃ 2-Cl-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1480 SO₂CH₃ 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 1481 SO₂CH₃ 2-Cl-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1482 SO₂CH₃ 2-Cl-phenyl 2-(amidinyl)phenyl 1483 SO₂CH₃ 2-Cl-phenyl 2-(N-guanidinyl)phenyl 1484 SO₂CH₃ 2-Cl-phenyl 2-(imidazolyl)phenyl 1485 SO₂CH₃ 2-Cl-phenyl 2-(imidazolidinyl)phenyl 1486 SO₂CH₃ 2-Cl-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1487 SO₂CH₃ 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 1488 SO₂CH₃ 2-Cl-phenyl 2-(2-piperidinyl)phenyl 1489 SO₂CH₃ 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 1490 SO₂CH₃ 2-Cl-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1491 SO₂CH₃ 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1492 SO₂CH₃ 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 1493 SO₂CH₃ 2-Cl-phenyl 2-(3-aminophenyl) 1494 SO₂CH₃ 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 1495 SO₂CH₃ 2-Cl-phenyl 2-glycinoyl 1496 SO₂CH₃ 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 1497 SO₂CH₃ 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1498 SO₂CH₃ 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl 1499 SO₂CH₃ 2-F-phenyl 2-(N-morpholino-methyl)phenyl 1500 SO₂CH₃ 2-F-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1501 SO₂CH₃ 2-F-phenyl 2-(N-Pyridinium-methyl)phenyl 1502 SO₂CH₃ 2-F-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1503 SO₂CH₃ 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 1504 SO₂CH₃ 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl 1505 SO₂CH₃ 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl 1506 SO₂CH₃ 2-F-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1507 SO₂CH₃ 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 1508 SO₂CH₃ 2-F-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1509 SO₂CH₃ 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 1510 SO₂CH₃ 2-F-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1511 SO₂CH₃ 2-F-phenyl 2-(amidinyl)phenyl 1512 SO₂CH₃ 2-F-phenyl 2-(N-guanidinyl)phenyl 1513 SO₂CH₃ 2-F-phenyl 2-(imidazolyl)phenyl 1514 SO₂CH₃ 2-F-phenyl 2-(imidazolidinyl)phenyl 1515 SO₂CH₃ 2-F-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1516 SO₂CH₃ 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 1517 SO₂CH₃ 2-F-phenyl 2-(2-piperidinyl)phenyl 1518 SO₂CH₃ 2-F-phenyl 2-(amidinyl-methyl)phenyl 1519 SO₂CH₃ 2-F-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1520 SO₂CH₃ 2-F-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1521 SO₂CH₃ 2-F-phenyl 2-dimethylaminoimidazol-1-yl 1522 SO₂CH₃ 2-F-phenyl 2-(3-aminophenyl) 1523 SO₂CH₃ 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 1524 SO₂CH₃ 2-F-phenyl 2-glycinoyl 1525 SO₂CH₃ 2-F-phenyl 2-(imidazol-1-ylacetyl) 1526 SO₂CH₃ 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1527 SO₂CH₃ 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 1528 SO₂CH₃ 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 1529 SO₂CH₃ 2,5-diF-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1530 SO₂CH₃ 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 1531 SO₂CH₃ 2,5-diF-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1532 SO₂CH₃ 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 1533 SO₂CH₃ 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 1534 SO₂CH₃ 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 1535 SO₂CH₃ 2,5-diF-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1536 SO₂CH₃ 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 1537 SO₂CH₃ 2,5-diF-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1538 SO₂CH₃ 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 1539 SO₂CH₃ 2,5-diF-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1540 SO₂CH₃ 2,5-diF-phenyl 2-(amidinyl)phenyl 1541 SO₂CH₃ 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 1542 SO₂CH₃ 2,5-diF-phenyl 2-(imidazolyl)phenyl 1543 SO₂CH₃ 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 1544 SO₂CH₃ 2,5-diF-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1545 SO₂CH₃ 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 1546 SO₂CH₃ 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 1547 SO₂CH₃ 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 1548 SO₂CH₃ 2,5-diF-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1549 SO₂CH₃ 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1550 SO₂CH₃ 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 1551 SO₂CH₃ 2,5-diF-phenyl 2-(3-aminophenyl) 1552 SO₂CH₃ 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 1553 SO₂CH₃ 2,5-diF-phenyl 2-glycinoyl 1554 SO₂CH₃ 2,5-diF-phenyl 2-(imidazol-1-ylacetyl) 1555 NHSO₂CH₃ phenyl 2-(aminosulfonyl)phenyl 1556 NHSO₂CH₃ phenyl 2-(methylaminosulfonyl)phenyl 1557 NHSO₂CH₃ phenyl 1-pyrrolidinocarbonyl 1558 NHSO₂CH₃ phenyl 2-(methylsulfonyl)phenyl 1559 NHSO₂CH₃ phenyl 4-morpholino 1560 NHSO₂CH₃ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1561 NHSO₂CH₃ phenyl 4-morpholinocarbonyl 1562 NHSO₂CH₃ 2-pyridyl 2-(aminosulfonyl)phenyl 1563 NHSO₂CH₃ 2-pyridyl 2-(methylaminosulfonyl)phenyl 1564 NHSO₂CH₃ 2-pyridyl 1-pyrrolidinocarbonyl 1565 NHSO₂CH₃ 2-pyridyl 2-(methylsulfonyl)phenyl 1566 NHSO₂CH₃ 2-pyridyl 4-morpholino 1567 NHSO₂CH₃ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1568 NHSO₂CH₃ 2-pyridyl 4-morpholinocarbonyl 1569 NHSO₂CH₃ 3-pyridyl 2-(aminosulfonyl)phenyl 1570 NHSO₂CH₃ 3-pyridyl 2-(methylaminosulfonyl)phenyl 1571 NHSO₂CH₃ 3-pyridyl 1-pyrrolidinocarbonyl 1572 NHSO₂CH₃ 3-pyridyl 2-(methylsulfonyl)phenyl 1573 NHSO₂CH₃ 3-pyridyl 4-morpholino 1574 NHSO₂CH₃ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1575 NHSO₂CH₃ 3-pyridyl 4-morpholinocarbonyl 1576 NHSO₂CH₃ 2-pyrimidyl 2-(aminosulfonyl)phenyl 1577 NHSO₂CH₃ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 1578 NHSO₂CH₃ 2-pyrimidyl 1-pyrrolidinocarbonyl 1579 NHSO₂CH₃ 2-pyrimidyl 2-(methylsulfonyl)phenyl 1580 NHSO₂CH₃ 2-pyrimidyl 4-morpholino 1581 NHSO₂CH₃ 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1582 NHSO₂CH₃ 2-pyrimidyl 4-morpholinocarbonyl 1583 NHSO₂CH₃ 5-pyrimidyl 2-(aminosulfonyl)phenyl 1584 NHSO₂CH₃ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 1585 NHSO₂CH₃ 5-pyrimidyl 1-pyrrolidinocarbonyl 1586 NHSO₂CH₃ 5-pyrimidyl 2-(methylsulfonyl)phenyl 1587 NHSO₂CH₃ 5-pyrimidyl 4-morpholino 1588 NHSO₂CH₃ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1589 NHSO₂CH₃ 5-pyrimidyl 4-morpholinocarbonyl 1590 NHSO₂CH₃ 2-Cl-phenyl 2-(aminosulfonyl)phenyl 1591 NHSO₂CH₃ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 1592 NHSO₂CH₃ 2-Cl-phenyl 1-pyrrolidinocarbonyl 1593 NHSO₂CH₃ 2-Cl-phenyl 2-(methylsulfonyl)phenyl 1594 NHSO₂CH₃ 2-Cl-phenyl 4-morpholino 1595 NHSO₂CH₃ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1596 NHSO₂CH₃ 2-Cl-phenyl 4-morpholinocarbonyl 1597 NHSO₂CH₃ 2-F-phenyl 2-(aminosulfonyl)phenyl 1598 NHSO₂CH₃ 2-F-phenyl 2-(methylaminosulfonyl)phenyl 1599 NHSO₂CH₃ 2-F-phenyl 1-pyrrolidinocarbonyl 1600 NHSO₂CH₃ 2-F-phenyl 2-(methylsulfonyl)phenyl 1601 NHSO₂CH₃ 2-F-phenyl 4-morpholino 1602 NHSO₂CH₃ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1603 NHSO₂CH₃ 2-F-phenyl 4-morpholinocarbonyl 1604 NHSO₂CH₃ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 1605 NHSO₂CH₃ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 1606 NHSO₂CH₃ 2,5-diF-phenyl 1-pyrrolidinocarbonyl 1607 NHSO₂CH₃ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 1608 NHSO₂CH₃ 2,5-diF-phenyl 4-morpholino 1609 NHSO₂CH₃ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 1610 NHSO₂CH₃ 2,5-diF-phenyl 4-morpholinocarbonyl 1611 NHSO₂CH₃ phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1612 NHSO₂CH₃ phenyl 2-(N-piperidinyl-methyl)phenyl 1613 NHSO₂CH₃ phenyl 2-(N-morpholino-methyl)phenyl 1614 NHSO₂CH₃ phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1615 NHSO₂CH₃ phenyl 2-(N-pyridinium-methyl)phenyl 1616 NHSO₂CH₃ phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1617 NHSO₂CH₃ phenyl 2-(N-azatanyl-methyl)phenyl 1618 NHSO₂CH₃ phenyl 2-(N-azetidinyl-methyl)phenyl 1619 NHSO₂CH₃ phenyl 2-(N-piperazinyl-methyl)phenyl 1620 NHSO₂CH₃ phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1621 NHSO₂CH₃ phenyl 2-(N-imidazolyl-methyl)phenyl 1622 NHSO₂CH₃ phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1623 NHSO₂CH₃ phenyl 2-(N-pyridonyl-methyl)phenyl 1624 NHSO₂CH₃ phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1625 NHSO₂CH₃ phenyl 2-(amidinyl)phenyl 1626 NHSO₂CH₃ phenyl 2-(N-guanidinyl)phenyl 1627 NHSO₂CH₃ phenyl 2-(imidazolyl)phenyl 1628 NHSO₂CH₃ phenyl 2-(imidazolidinyl)phenyl 1629 NHSO₂CH₃ phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1630 NHSO₂CH₃ phenyl 2-(2-pyrrolidinyl)phenyl 1631 NHSO₂CH₃ phenyl 2-(2-piperidinyl)phenyl 1632 NHSO₂CH₃ phenyl 2-(amidinyl-methyl)phenyl 1633 NHSO₂CH₃ phenyl 2-(2-imidazolidinyl-methyl)phenyl 1634 NHSO₂CH₃ phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1635 NHSO₂CH₃ phenyl 2-dimethylaminoimidazol-1-yl 1636 NHSO₂CH₃ phenyl 2-(3-aminophenyl) 1637 NHSO₂CH₃ phenyl 2-(3-pyrrolidinylcarbonyl) 1638 NHSO₂CH₃ phenyl 2-glycinoyl 1639 NHSO₂CH₃ phenyl 2-(imidazol-1-ylacetyl) 1640 NHSO₂CH₃ 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1641 NHSO₂CH₃ 2-pyridyl 2-(N-piperidinyl-methyl)phenyl 1642 NHSO₂CH₃ 2-pyridyl 2-(N-morpholino-methyl)phenyl 1643 NHSO₂CH₃ 2-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1644 NHSO₂CH₃ 2-pyridyl 2-(N-pyridinium-methyl)phenyl 1645 NHSO₂CH₃ 2-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1646 NHSO₂CH₃ 2-pyridyl 2-(N-azatanyl-methyl)phenyl 1647 NHSO₂CH₃ 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 1648 NHSO₂CH₃ 2-pyridyl 2-(N-piperazinyl-methyl)phenyl 1649 NHSO₂CH₃ 2-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1650 NHSO₂CH₃ 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 1651 NHSO₂CH₃ 2-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1652 NHSO₂CH₃ 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 1653 NHSO₂CH₃ 2-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1654 NHSO₂CH₃ 2-pyridyl 2-(amidinyl)phenyl 1655 NHSO₂CH₃ 2-pyridyl 2-(N-guanidinyl)phenyl 1656 NHSO₂CH₃ 2-pyridyl 2-(imidazolyl)phenyl 1657 NHSO₂CH₃ 2-pyridyl 2-(imidazolidinyl)phenyl 1658 NHSO₂CH₃ 2-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1659 NHSO₂CH₃ 2-pyridyl 2-(2-pyrrolidinyl)phenyl 1660 NHSO₂CH₃ 2-pyridyl 2-(2-piperidinyl)phenyl 1661 NHSO₂CH₃ 2-pyridyl 2-(amidinyl-methyl)phenyl 1662 NHSO₂CH₃ 2-pyridyl 2-(2-imidazolidinyl-methyl)phenyl 1663 NHSO₂CH₃ 2-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1664 NHSO₂CH₃ 2-pyridyl 2-dimethylaminoimidazol-1-yl 1665 NHSO₂CH₃ 2-pyridyl 2-(3-aminophenyl) 1666 NHSO₂CH₃ 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 1667 NHSO₂CH₃ 2-pyridyl 2-glycinoyl 1668 NHSO₂CH₃ 2-pyridyl 2-(imidazol-1-ylacetyl) 1669 NHSO₂CH₃ 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1670 NHSO₂CH₃ 3-pyridyl 2-(N-piperidinyl-methyl)phenyl 1671 NHSO₂CH₃ 3-pyridyl 2-(N-morpholino-methyl)phenyl 1672 NHSO₂CH₃ 3-pyridyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1673 NHSO₂CH₃ 3-pyridyl 2-(N-pyridinium-methyl)phenyl 1674 NHSO₂CH₃ 3-pyridyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1675 NHSO₂CH₃ 3-pyridyl 2-(N-azatanyl-methyl)phenyl 1676 NHSO₂CH₃ 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 1677 NHSO₂CH₃ 3-pyridyl 2-(N-piperazinyl-methyl)phenyl 1678 NHSO₂CH₃ 3-pyridyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1679 NHSO₂CH₃ 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 1680 NHSO₂CH₃ 3-pyridyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1681 NHSO₂CH₃ 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 1682 NHSO₂CH₃ 3-pyridyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1683 NHSO₂CH₃ 3-pyridyl 2-(amidinyl)phenyl 1684 NHSO₂CH₃ 3-pyridyl 2-(N-guanidinyl)phenyl 1685 NHSO₂CH₃ 3-pyridyl 2-(imidazolyl)phenyl 1686 NHSO₂CH₃ 3-pyridyl 2-(imidazolidinyl)phenyl 1687 NHSO₂CH₃ 3-pyridyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1688 NHSO₂CH₃ 3-pyridyl 2-(2-pyrrolidinyl)phenyl 1689 NHSO₂CH₃ 3-pyridyl 2-(2-piperidinyl)phenyl 1690 NHSO₂CH₃ 3-pyridyl 2-(amidinyl-methyl)phenyl 1691 NHSO₂CH₃ 3-pyridyl 2-(2-imidazolidinyl-methyl)phenyl 1692 NHSO₂CH₃ 3-pyridyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1693 NHSO₂CH₃ 3-pyridyl 2-dimethylaminoimidazol-1-yl 1694 NHSO₂CH₃ 3-pyridyl 2-(3-aminophenyl) 1695 NHSO₂CH₃ 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 1696 NHSO₂CH₃ 3-pyridyl 2-glycinoyl 1697 NHSO₂CH₃ 3-pyridyl 2-(imidazol-1-ylacetyl) 1698 NHSO₂CH₃ 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 1699 NHSO₂CH₃ 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl 1700 NHSO₂CH₃ 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 1701 NHSO₂CH₃ 2-pyrimidyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1702 NHSO₂CH₃ 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 1703 NHSO₂CH₃ 2-pyrimidyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1704 NHSO₂CH₃ 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 1705 NHSO₂CH₃ 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl 1706 NHSO₂CH₃ 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl 1707 NHSO₂CH₃ 2-pyrimidyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1708 NHSO₂CH₃ 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 1709 NHSO₂CH₃ 2-pyrimidyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1710 NHSO₂CH₃ 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 1711 NHSO₂CH₃ 2-pyrimidyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1712 NHSO₂CH₃ 2-pyrimidyl 2-(amidinyl)phenyl 1713 NHSO₂CH₃ 2-pyrimidyl 2-(N-guanidinyl)phenyl 1714 NHSO₂CH₃ 2-pyrimidyl 2-(imidazolyl)phenyl 1715 NHSO₂CH₃ 2-pyrimidyl 2-(imidazolidinyl)phenyl 1716 NHSO₂CH₃ 2-pyrimidyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1717 NHSO₂CH₃ 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl 1718 NHSO₂CH₃ 2-pyrimidyl 2-(2-piperidinyl)phenyl 1719 NHSO₂CH₃ 2-pyrimidyl 2-(amidinyl-methyl)phenyl 1720 NHSO₂CH₃ 2-pyrimidyl 2-(2-imidazolidinyl-methyl)phenyl 1721 NHSO₂CH₃ 2-pyrimidyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1722 NHSO₂CH₃ 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 1723 NHSO₂CH₃ 2-pyrimidyl 2-(3-aminophenyl) 1724 NHSO₂CH₃ 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 1725 NHSO₂CH₃ 2-pyrimidyl 2-glycinoyl 1726 NHSO₂CH₃ 2-pyrimidyl 2-(imidazol-1-ylacetyl) 1727 NHSO₂CH₃ 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1728 NHSO₂CH₃ 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl 1729 NHSO₂CH₃ 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 1730 NHSO₂CH₃ 2-Cl-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1731 NHSO₂CH₃ 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 1732 NHSO₂CH₃ 2-Cl-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1733 NHSO₂CH₃ 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 1734 NHSO₂CH₃ 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl 1735 NHSO₂CH₃ 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl 1736 NHSO₂CH₃ 2-Cl-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1737 NHSO₂CH₃ 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 1738 NHSO₂CH₃ 2-Cl-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1739 NHSO₂CH₃ 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 1740 NHSO₂CH₃ 2-Cl-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1741 NHSO₂CH₃ 2-Cl-phenyl 2-(amidinyl)phenyl 1742 NHSO₂CH₃ 2-Cl-phenyl 2-(N-guanidinyl)phenyl 1743 NHSO₂CH₃ 2-Cl-phenyl 2-(imidazolyl)phenyl 1744 NHSO₂CH₃ 2-Cl-phenyl 2-(imidazolidinyl)phenyl 1745 NHSO₂CH₃ 2-Cl-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1746 NHSO₂CH₃ 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 1747 NHSO₂CH₃ 2-Cl-phenyl 2-(2-piperidinyl)phenyl 1748 NHSO₂CH₃ 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 1749 NHSO₂CH₃ 2-Cl-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1750 NHSO₂CH₃ 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1751 NHSO₂CH₃ 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 1752 NHSO₂CH₃ 2-Cl-phenyl 2-(3-aminophenyl) 1753 NHSO₂CH₃ 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 1754 NHSO₂CH₃ 2-Cl-phenyl 2-glycinoyl 1755 NHSO₂CH₃ 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 1756 NHSO₂CH₃ 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1757 NHSO₂CH₃ 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl 1758 NHSO₂CH₃ 2-F-phenyl 2-(N-morpholino-methyl)phenyl 1759 NHSO₂CH₃ 2-F-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1760 NHSO₂CH₃ 2-F-phenyl 2-(N-pyridinium-methyl)phenyl 1761 NHSO₂CH₃ 2-F-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1762 NHSO₂CH₃ 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 1763 NHSO₂CH₃ 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl 1764 NHSO₂CH₃ 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl 1765 NHSO₂CH₃ 2-F-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1766 NHSO₂CH₃ 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 1767 NHSO₂CH₃ 2-F-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1768 NHSO₂CH₃ 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 1769 NHSO₂CH₃ 2-F-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1770 NHSO₂CH₃ 2-F-phenyl 2-(amidinyl)phenyl 1771 NHSO₂CH₃ 2-F-phenyl 2-(N-guanidinyl)phenyl 1772 NHSO₂CH₃ 2-F-phenyl 2-(imidazolyl)phenyl 1773 NHSO₂CH₃ 2-F-phenyl 2-(imidazolidinyl)phenyl 1774 NHSO₂CH₃ 2-F-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1775 NHSO₂CH₃ 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 1776 NHSO₂CH₃ 2-F-phenyl 2-(2-piperidinyl)phenyl 1777 NHSO₂CH₃ 2-F-phenyl 2-(amidinyl-methyl)phenyl 1778 NHSO₂CH₃ 2-F-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1779 NHSO₂CH₃ 2-F-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1780 NHSO₂CH₃ 2-F-phenyl 2-dimethylaminoimidazol-1-yl 1781 NHSO₂CH₃ 2-F-phenyl 2-(3-aminophenyl) 1782 NHSO₂CH₃ 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 1783 NHSO₂CH₃ 2-F-phenyl 2-glycinoyl 1784 NHSO₂CH₃ 2-F-phenyl 2-(imidazol-1-ylacetyl) 1785 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1786 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 1787 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 1788 NHSO₂CH₃ 2,5-diF-phenyl 2-(N,N′-methylmorpholinium-methyl)phenyl 1789 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 1790 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-4-(N,N′-dimethylamino)-pyridinium-methyl)phenyl 1791 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 1792 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 1793 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 1794 NHSO₂CH₃ 2,5-diF-phenyl 2-(N,N′-BOC-piperazinyl-methyl)phenyl 1795 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 1796 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-methoxy-N-methylamino-methyl)phenyl 1797 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 1798 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-(N′,N′-dimethylhydrazinyl-methyl)phenyl 1799 NHSO₂CH₃ 2,5-diF-phenyl 2-(amidinyl)phenyl 1800 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 1801 NHSO₂CH₃ 2,5-diF-phenyl 2-(imidazolyl)phenyl 1802 NHSO₂CH₃ 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 1803 NHSO₂CH₃ 2,5-diF-phenyl 2-(2-imidazolidinyl-sulfonyl)phenyl 1804 NHSO₂CH₃ 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 1805 NHSO₂CH₃ 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 1806 NHSO₂CH₃ 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 1807 NHSO₂CH₃ 2,5-diF-phenyl 2-(2-imidazolidinyl-methyl)phenyl 1808 NHSO₂CH₃ 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)-methyl)phenyl 1809 NHSO₂CH₃ 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 1810 NHSO₂CH₃ 2,5-diF-phenyl 2-(3-aminophenyl) 1811 NHSO₂CH₃ 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 1812 NHSO₂CH₃ 2,5-diF-phenyl 2-glycinoyl 1813 NHSO₂CH₃ 2,5-diF-phenyl 2-(imidazol-1-ylacetyl)

TABLE 3

a₁ R = F, D = NH₂ b₁ R = F, D = NH₂ c₁ R = F, D = NH₂ a₂ R = H, D = NH₂ b₂ R = H, D = NH₂ c₂ R = H, D = NH₂ a₃ R = F, D = CH₂NH₂ b₃ R = F, D = CH₂NH₂ c₃ R = F, D = CH₂NH₂ a₄ R = H, D = CH₂NH₂ b₄ R = H, D = CH₂NH₂ c₄ R = H, D = CH₂NH₂ a₅ R = F, D = C(═NH)NH₂ b₅ R = F, D = C(═NH)NH₂ c₅ R = F, D = C(═NH)NH₂ a₆ R = H, D = C(═NH)NH₂ b₆ R = H, D = C(═NH)NH₂ c₆ R = H, D = C(═NH)NH₂ a₇ R = F, D = C(O)NH₂ b₇ R = F, D = C(O)NH₂ c₇ R = F, D = C(O)NH₂ a₈ R = H, D = C(O)NH₂ b₈ R = H, D = C(O)NH₂ c₈ R = H, D = C(O)NH₂

d₁ R = F, D = NH₂ e₁ R = F, D = NH₂ f₁ R = F, D = NH₂ d₂ R = H, D = NH₂ e₂ R = H, D = NH₂ f₂ R = H, D = NH₂ d₃ R = F, D = CH₂NH₂ e₃ R = F, D = CH₂NH₂ f₃ R = F, D = CH₂NH₂ d₄ R = H, D = CH₂NH₂ e₄ R = H, D = CH₂NH₂ f₄ R = H, D = CH₂NH₂ d₅ R = F, D = C(═NH)NH₂ e₅ R = F, D = C(═NH)NH₂ f₅ R = F, D = C(═NH)NH₂ d₆ R = H, D = C(═NH)NH₂ e₆ R = H, D = C(═NH)NH₂ f₆ R = H, D = C(═NH)NH₂ d₇ R = F, D = C(O)NH₂ e₇ R = F, D = C(O)NH₂ f₇ R = F, D = C(O)NH₂ d₈ R = H, D = C(O)NH₂ e₈ R = H, D = C(O)NH₂ f₈ R = H, D = C(O)NH₂

g₁ R = F, D = NH₂ h₁ R = F, D = NH₂ i₁ R = F, D = NH₂ g₂ R = H, D = NH₂ h₂ R = H, D = NH₂ i₂ R = H, D = NH₂ g₃ R = F, D = CH₂NH₂ h₃ R = F, D = CH₂NH₂ i₃ R = F, D = CH₂NH₂ g₄ R = H, D = CH₂NH₂ h₄ R = H, D = CH₂NH₂ i₄ R = H, D = CH₂NH₂ g₅ R = F, D = C(═NH)NH₂ h₅ R = F, D = C(═NH)NH₂ i₅ R = F, D = C(═NH)NH₂ g₆ R = H, D = C(═NH)NH₂ h₆ R = H, D = C(═NH)NH₂ i₆ R = H, D = C(═NH)NH₂ g₇ R = F, D = C(O)NH₂ h₇ R = F, D = C(O)NH₂ i₇ R = F, D = C(O)NH₂ g₈ R = H, D = C(O)NH₂ h₈ R = H, D = C(O)NH₂ i₈ R = H, D = C(O)NH₂

j₁ R = F, D = NH₂ k₁ R = F, D = NH₂ l₁ R = F, D = NH₂ j₂ R = H, D = NH₂ k₂ R = H, D = NH₂ l₂ R = H, D = NH₂ j₃ R = F, D = CH₂NH₂ k₃ R = F, D = CH₂NH₂ l₃ R = F, D = CH₂NH₂ j₄ R = H, D = CH₂NH₂ k₄ R = H, D = CH₂NH₂ l₄ R = H, D = CH₂NH₂ j₅ R = F, D = C(═NH)NH₂ k₅ R = F, D = C(═NH)NH₂ l₆ R = F, D = C(═NH)NH₂ j₆ R = H, D = C(═NH)NH₂ k₆ R = H, D = C(═NH)NH₂ l₆ R = H, D = C(═NH)NH₂ j₇ R = F, D = C(O)NH₂ k₇ R = F, D = C(O)NH₂ l₇ R = F, D = C(O)NH₂ j₈ R = H, D = C(O)NH₂ k₈ R = H, D = C(O)NH₂ l₈ R = H, D = C(O)NH₂

m₁ R = F, D = NH₂ n₁ R = F, D = NH₂ o₁ R = F, D = NH₂ m₂ R = H, D = NH₂ n₂ R = H, D = NH₂ o₂ R = H, D = NH₂ m₃ R = F, D = CH₂NH₂ n₃ R = F, D = CH₂NH₂ o₃ R = F, D = CH₂NH₂ m₄ R = H, D = CH₂NH₂ n₄ R = H, D = CH₂NH₂ o₄ R = H, D = CH₂NH₂ m₅ R = F, D = C(═NH)NH₂ n₅ R = F, D = C(═NH)NH₂ o₅ R = F, D = C(═NH)NH₂ m₆ R = H, D = C(═NH)NH₂ n₆ R = H, D = C(═NH)NH₂ o₆ R = H, D = C(═NH)NH₂ m₇ R = F, D = C(O)NH₂ n₇ R = F, D = C(O)NH₂ o₇ R = F, D = C(O)NH₂ m₈ R = H, D = C(O)NH₂ n₈ R = H, D = C(O)NH₂ o₈ R = H, D = C(O)NH₂

p₁ R = F, D = NH₂ q₁ R = F, D = NH₂ r₁ R = F, D = NH₂ p₂ R = Cl, D = NH₂ q₂ R = Cl, D = NH₂ r₂ R = Cl, D = NH₂ p₃ R = OMe, D = NH₂ q₃ R = OMe, D = NH₂ r₃ R = OMe, D = NH₂ p₄ R = F, D = CH₂NH₂ q₄ R = F, D = CH₂NH₂ r₄ R = F, D = CH₂NH₂ p₅ R = Cl, D = CH₂NH₂ q₅ R = Cl, D = CH₂NH₂ r₅ R = Cl, D = CH₂NH₂ p₆ R = OMe, D = CH₂NH₂ q₆ R = OMe, D = CH₂NH₂ r₆ R = OMe, D = CH₂NH₂ p₇ R = F, D = C(═NH)NH₂ q₇ R = F, D = C(═NH)NH₂ r₇ R = F, D = C(═NH)NH₂ p₈ R = Cl, D = C(═NH)NH₂ q₈ R = Cl, D = C(═NH)NH₂ r₈ R = Cl, D = C(═NH)NH₂ p₉ R = OMe, D = C(═NH)NH₂ q₉ R = OMe, D = C(═NH)NH₂ r₉ R = OMe, D = C(═NH)NH₂ p₁₀ R = F, D = C(O)NH₂ q₁₀ R = F, D = C(O)NH₂ r₁₀ R = F, D = C(O)NH₂ p₁₁ R = Cl, D = C(O)NH₂ q₁₁ R = Cl, D = C(O)NH₂ r₁₁ R = Cl, D = C(O)NH₂ p₁₂ R = OMe, D = C(O)NH₂ q₁₂ R = OMe, D = C(O)NH₂ r₁₂ R = OMe, D = C(O)NH₂

s₁ R = F, D = NH₂ t₁ R = F, D = NH₂ u₁ R = F, D = NH₂ s₂ R = Cl, D = NH₂ t₂ R = Cl, D = NH₂ u₂ R = Cl, D = NH₂ s₃ R = OMe, D = NH₂ t₃ R = OMe, D = NH₂ u₃ R = OMe, D = NH₂ s₄ R = F, D = CH₂NH₂ t₄ R = F, D = CH₂NH₂ u₄ R = F, D = CH₂NH₂ s₅ R = Cl, D = CH₂NH₂ t₅ R = Cl, D = CH₂NH₂ u₅ R = Cl, D = CH₂NH₂ s₆ R = OMe, D = CH₂NH₂ t₆ R = OMe, D = CH₂NH₂ u₆ R = OMe, D = CH₂NH₂ s₇ R = F, D = C(═NH)NH₂ t₇ R = F, D = C(═NH)NH₂ u₇ R = F, D = C(═NH)NH₂ s₈ R = Cl, D = C(═NH)NH₂ t₈ R = Cl, D = C(═NH)NH₂ u₈ R = Cl, D = C(═NH)NH₂ s₉ R = OMe, D = C(═NH)NH₂ t₉ R = OMe, D = C(═NH)NH₂ u₉ R = OMe, D = C(═NH)NH₂ s₁₀ R = F, D = C(O)NH₂ t₁₀ R = F, D = C(O)NH₂ u₁₀ R = F, D = C(O)NH₂ s₁₁ R = Cl, D = C(O)NH₂ t₁₁ R = Cl, D = C(O)NH₂ u₁₁ R = Cl, D = C(O)NH₂ s₁₂ R = OMe, D = C(O)NH₂ t₁₂ R = OMe, D = C(O)NH₂ u₁₂ R = OMe, D = C(O)NH₂

v₁ R = F, D = NH₂ w₁ R = F, D = NH₂ x₁ R = F, D = NH₂ v₂ R = Cl, D = NH₂ w₂ R = Cl, D = NH₂ x₂ R = Cl, D = NH₂ v₃ R = OMe, D = NH₂ w₃ R = OMe, D = NH₂ x₃ R = OMe, D = NH₂ v₄ R = F, D = CH₂NH₂ w₄ R = F, D = CH₂NH₂ x₄ R = F, D = CH₂NH₂ v₅ R = Cl, D = CH₂NH₂ w₅ R = Cl, D = CH₂NH₂ x₅ R = Cl, D = CH₂NH₂ v₆ R = OMe, D = CH₂NH₂ w₆ R = OMe, D = CH₂NH₂ x₆ R = OMe, D = CH₂NH₂ v₇ R = F, D = C(═NH)NH₂ w₇ R = F, D = C(═NH)NH₂ x₇ R = F, D = C(═NH)NH₂ v₈ R = Cl, D = C(═NH)NH₂ w₈ R = Cl, D = C(═NH)NH₂ x₈ R = Cl, D = C(═NH)NH₂ v₉ R = OMe, D = C(═NH)NH₂ w₉ R = OMe, D = C(═NH)NH₂ x₉ R = OMe, D = C(═NH)NH₂ v₁₀ R = F, D = C(O)NH₂ w₁₀ R = F, D = C(O)NH₂ x₁₀ R = F, D = C(O)NH₂ v₁₁ R = Cl, D = C(O)NH₂ w₁₁ R = Cl, D = C(O)NH₂ x₁₁ R = Cl, D = C(O)NH₂ v₁₂ R = OMe, D = C(O)NH₂ w₁₂ R = OMe, D = C(O)NH₂ x₁₂ R = OMe, D = C(O)NH₂

y₁ R = F, D = NH₂ z₁ R = F, D = NH₂ aa₁ R = F, D = NH₂ y₂ R = Cl, D = NH₂ z₂ R = Cl, D = NH₂ aa₂ R = Cl, D = NH₂ y₃ R = OMe, D = NH₂ z₃ R = OMe, D = NH₂ aa₃ R = OMe, D = NH₂ y₄ R = F, D = CH₂NH₂ z₄ R = F, D = CH₂NH₂ aa₄ R = F, D = CH₂NH₂ y₅ R = Cl, D = CH₂NH₂ z₅ R = Cl, D = CH₂NH₂ aa₅ R = Cl, D = CH₂NH₂ y₆ R = OMe, D = CH₂NH₂ z₆ R = OMe, D = CH₂NH₂ aa₆ R = OMe, D = CH₂NH₂ y₇ R = F, D = C(═NH)NH₂ z₇ R = F, D = C(═NH)NH₂ aa₇ R = F, D = C(═NH)NH₂ y₈ R = Cl, D = C(═NH)NH₂ z₈ R = Cl, D = C(═NH)NH₂ aa₈ R = Cl, D = C(═NH)NH₂ y₉ R = OMe, D = C(═NH)NH₂ z₉ R = OMe, D = C(═NH)NH₂ aa₉ R = OMe, D = C(═NH)NH₂ y₁₀ R = F, D = C(O)NH₂ z₁₀ R = F, D = C(O)NH₂ aa₁₀ R = F, D = C(O)NH₂ y₁₁ R = Cl, D = C(O)NH₂ z₁₁ R = Cl, D = C(O)NH₂ aa₁₁ R = Cl, D = C(O)NH₂ y₁₂ R = OMe, D = C(O)NH₂ z₁₂ R = OMe, D = C(O)NH₂ aa₁₂ R = OMe, D = C(O)NH₂

bb₁ R = F, D = NH₂ cc₁ R = F, D = NH₂ dd₁ R = F, D = NH₂ bb₂ R = Cl, D = NH₂ cc₂ R = Cl, D = NH₂ dd₂ R = Cl, D = NH₂ bb₃ R = OMe, D = NH₂ cc₃ R = OMe, D = NH₂ dd₃ R = OMe, D = NH₂ bb₄ R = F, D = CH₂NH₂ cc₄ R = F, D = CH₂NH₂ dd₄ R = F, D = CH₂NH₂ bb₅ R = Cl, D = CH₂NH₂ cc₅ R = Cl, D = CH₂NH₂ dd₅ R = Cl, D = CH₂NH₂ bb₆ R = OMe, D = CH₂NH₂ cc₆ R = OMe, D = CH₂NH₂ dd₆ R = OMe, D = CH₂NH₂ bb₇ R = F, D = C(═NH)NH₂ cc₇ R = F, D = C(═NH)NH₂ dd₇ R = F, D = C(═NH)NH₂ bb₈ R = Cl, D = C(═NH)NH₂ cc₈ R = Cl, D = C(═NH)NH₂ dd₈ R = Cl, D = C(═NH)NH₂ bb₉ R = OMe, D = C(═NH)NH₂ cc₉ R = OMe, D = C(═NH)NH₂ dd₉ R = OMe, D = C(═NH)NH₂ bb₁₀ R = F, D = C(O)NH₂ cc₁₀ R = F, D = C(O)NH₂ dd₁₀ R = F, D = C(O)NH₂ bb₁₁ R = Cl, D = C(O)NH₂ cc₁₁ R = Cl, D = C(O)NH₂ dd₁₁ R = Cl, D = C(O)NH₂ bb₁₂ R = OMe, D = C(O)NH₂ cc₁₂ R = OMe, D = C(O)NH₂ dd₁₂ R = OMe, D = C(O)NH₂

ee₁ R = F, D = CH₂NH₂ ff₁ R = F, D = CH₂NH₂ gg₁ R = F, D = CH₂NH₂ ee₂ R = Cl, D = CH₂NH₂ ff₂ R = Cl, D = CH₂NH₂ gg₂ R = Cl, D = CH₂NH₂ ee₃ R = OMe, D = CH₂NH₂ ff₃ R = OMe, D = CH₂NH₂ gg₃ R = OMe, D = CH₂NH₂ ee₄ R = CH₂NH₂, D = CH₂NH₂ ff₄ R = CH₂NH₂, D = CH₂NH₂ gg₄ R = CH₂NH₂, D = CH₂NH₂

hh₁ R = F, D = CH₂NH₂ ii₁ R = F, D = CH₂NH₂ jj₁ R = F, D = CH₂NH₂ hh₂ R = Cl, D = CH₂NH₂ ii₂ R = Cl, D = CH₂NH₂ jj₂ R = Cl, D = CH₂NH₂ hh₃ R = OMe, D = CH₂NH₂ ii₃ R = OMe, D = CH₂NH₂ jj₃ R = OMe, D = CH₂NH₂ hh₄ R = CH₂NH₂, D = CH₂NH₂ ii₄ R = CH₂NH₂, D = CH₂NH₂ jj₄ R = CH₂NH₂, D = CH₂NH₂

kk₁ R = F, D = CH₂NH₂ ll₁ R = F, D = CH₂NH₂ mm₁ R = F, D = CH₂NH₂ kk₂ R = Cl, D = CH₂NH₂ ll₂ R = Cl, D = CH₂NH₂ mm₂ R = Cl, D = CH₂NH₂ kk₃ R = OMe, D = CH₂NH₂ ll₃ R = OMe, D = CH₂NH₂ mm₃ R = OMe, D = CH₂NH₂ kk₄ R = CH₂NH₂, D = CH₂NH₂ ll₄ R = CH₂NH₂, D = CH₂NH₂ mm₄ R = CH₂NH₂, D = CH₂NH₂

nn₁ R = F, D = CH₂NH₂ oo₁ R = F, D = CH₂NH₂ pp₁ R = F, D = CH₂NH₂ nn₂ R = Cl, D = CH₂NH₂ oo₂ R = Cl, D = CH₂NH₂ pp₂ R = Cl, D = CH₂NH₂ nn₃ R = OMe, D = CH₂NH₂ oo₃ R = OMe, D = CH₂NH₂ pp₃ R = OMe, D = CH₂NH₂ nn₄ R = CH₂NH₂, D = CH₂NH₂ oo₄ R = CH₂NH₂, D = CH₂NH₂ pp₄ R = CH₂NH₂, D = CH₂NH₂

qq₁ R = F, D = CH₂NH₂ rr₁ R = F, D = CH₂NH₂ ss₁ R = F, D = CH₂NH₂ qq₂ R = Cl, D = CH₂NH₂ rr₂ R = Cl, D = CH₂NH₂ ss₂ R = Cl, D = CH₂NH₂ qq₃ R = OMe, D = CH₂NH₂ rr₃ R = OMe, D = CH₂NH₂ ss₃ R = OMe, D = CH₂NH₂ qq₄ R = CH₂NH₂, D = CH₂NH₂ rr₄ R = CH₂NH₂, D = CH₂NH₂ ss₄ R = CH₂NH₂, D = CH₂NH₂ Ex # R^(1b) A B  1 H phenyl 2-((Me)₂N-methyl)phenyl  2 H phenyl 2-((Me)NH-methyl)phenyl  3 H phenyl 2-(H₂N-methyl)phenyl  4 H phenyl 2-HOCH₂-phenyl  5 H 2-F-phenyl 2-((Me)₂N-methyl)phenyl  6 H 2-F-phenyl 2-((Me)NH-methyl)phenyl  7 H 2-F-phenyl 2-(H₂N-methyl)phenyl  8 H 2-F-phenyl 2-HOCH₂-phenyl  9 H phenyl 2-methylimidazol-1-yl  10 H phenyl 2-ethylimidazol-1-yl  11 H phenyl 2-((Me)₂N-methyl)imidazol-1-yl  12 H phenyl 2-CH₃SO₂-imidazol-1-yl  13 H phenyl 2-CH₃OCH₂-imidazol-1-yl  14 H 2-F-phenyl 2-methylimidazol-1-yl  15 H 2-F-phenyl 2-ethylimidazol-1-yl  16 H 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  17 H 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl  18 H 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl  19 H 2-Cl-phenyl 2-methylimidazol-1-yl  20 H 2-Cl-phenyl 2-ethylimidazol-1-yl  21 H 2-Cl-phenyl 2- ((Me)₂N-methyl)imidazol-1-yl  22 H 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl  23 H 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl  24 H 2-(Me)₂N-phenyl 2-methylimidazol-1-yl  25 H 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl  26 H 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  27 H 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl  28 H 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl  29 H phenyl N-methylimidazol-2-yl  30 H phenyl 4-methylimidazol-5-yl  31 H phenyl 5-CF₃-pyrazol-1-yl  32 H 2-F-phenyl N-methylimidazol-2-yl  33 H 2-F-phenyl 4-methylimidazol-5-yl  34 H 2-F-phenyl 5-CF₃-pyrazol-1-yl  35 H phenyl guanidino  36 H phenyl 2-thiazolin-2-ylamine  37 H phenyl N-methyl-2-imidazolin-2-yl  38 H phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl  39 H phenyl N-methylimidazol-2-ylthiol  40 H phenyl t-butoxycarbonylamine  41 H phenyl (N-pyrrolidino)formylimino  42 H phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino  43 H 2-F-phenyl guanidino  44 H 2-F-phenyl 2-thiazolin-2-ylamine  45 H 2-F-phenyl N-methyl-2-imidazolin-2-yl  46 H 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl  47 H 2-F-phenyl N-methylimidazol-2-ylthio  48 H 2-F-phenyl t-butoxycarbonylamine  49 H 2-F-phenyl (N-pyrrolidino)formylimino  50 H 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino  51 H 2-CH₃O-phenyl (N-pyrrolidino)formylimino  52 H 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino  53 —CN phenyl 2-((Me)₂N-methyl)phenyl  54 —CN phenyl 2-((Me)NH-methyl)phenyl  55 —CN phenyl 2-(H₂N-methyl)phenyl  56 —CN phenyl 2-HOCH₂-phenyl  57 —CN 2-F-phenyl 2-((Me)₂N-methyl)phenyl  58 —CN 2-F-phenyl 2-((Me)NH-methyl)phenyl  59 —CN 2-F-phenyl 2-(H₂N-methyl)phenyl  60 —CN 2-F-phenyl 2-HOCH₂-phenyl  61 —CN phenyl 2-methylimidazol-1-yl  62 —CN phenyl 2-ethylimidazol-1-yl  63 —CN phenyl 2-((Me)₂N-methyl)imidazol-1-yl  64 —CN phenyl 2-CH₃SO₂-imidazol-1-yl  65 —CN phenyl 2-CH₃OCH₂-imidazol-1-yl  66 —CN 2-F-phenyl 2-methylimidazol-1-yl  67 —CN 2-F-phenyl 2-ethylimidazol-1-yl  68 —CN 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  69 —CN 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl  70 —CN 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl  71 —CN 2-Cl-phenyl 2-methylimidazol-1-yl  72 —CN 2-Cl-phenyl 2-ethylimidazol-1-yl  73 —CN 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  74 —CN 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl  75 —CN 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl  76 —CN 2-(Me)₂N-phenyl 2-methylimidazol-1-yl  77 —CN 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl  78 —CN 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  79 —CN 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl  80 —CN 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl  81 —CN phenyl N-methylimidazol-2-yl  82 —CN phenyl 4-methylimidazol-5-yl  83 —CN phenyl 5-CF₃-pyrazol-1-yl  84 —CN 2-F-phenyl N-methylimidazol-2-yl  85 —CN 2-F-phenyl 4-methylimidazol-5-yl  86 —CN 2-F-phenyl 5-CF₃-pyrazol-1-yl  87 —CN phenyl guanidino  88 —CN phenyl 2-thiazolin-2-ylamine  89 —CN phenyl N-methyl-2-imidazolin-2-yl  90 —CN phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl  91 —CN phenyl N-methylimidazol-2-ylthiol  92 —CN phenyl t-butoxycarbonylamine  93 —CN phenyl (N-pyrrolidino)formylimino  94 —CN phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino  95 —CN 2-F-phenyl guanidind  96 —CN 2-F-phenyl 2-thiazolin-2-ylamine  97 —CN 2-F-phenyl N-methyl-2-imidazolin-2-yl  98 —CN 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl  99 —CN 2-F-phenyl N-methylimidazol-2-ylthio 100 —CN 2-F-phenyl t-butoxycarbonylamine 101 —CN 2-F-phenyl (N-pyrrolidino)formylimino 102 —CN 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 103 —CN 2-CH₃O-phenyl (N-pyrrolidino)formylimino 104 —CN 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 105 CF₃ phenyl 2-((Me)₂N-methyl)phenyl 106 CF₃ phenyl 2-((Me)NH-methyl)phenyl 107 CF₃ phenyl 2-(H₂N-methyl)phenyl 108 CF₃ phenyl 2-HOCH₂-phenyl 109 CF₃ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 110 CF₃ 2-F-phenyl 2-((Me)NH-methyl)phenyl 111 CF₃ 2-F-phehyl 2-(H₂N-methyl )phenyl 112 CF₃ 2-F-phenyl 2-HOCH₂-phenyl 113 CF₃ phenyl 2-methylimidazol-1-yl 114 CF₃ phenyl 2-ethylimidazol-1-yl 115 CF₃ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 116 CF₃ phenyl 2-CH₃SO₂-imidazol-1-yl 117 CF₃ phenyl 2-CH₃OCH₂-imidazol-1-yl 118 CF₃ 2-F-phenyl 2-methylimidazol-1-y1 119 CF₃ 2-F-phenyl 2-ethylimidazol-1-yl 120 CF₃ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 121 CF₃ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 122 CF₃ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 123 CF₃ 2-Cl-phenyl 2-methylimidazol-1-yl 124 CF₃ 2-Cl-phenyl 2-ethylimidazol-1-yl 125 CF₃ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 126 CF₃ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 127 CF₃ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 128 CF₃ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 129 CF₃ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 130 CF₃ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 131 CF₃ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 132 CF₃ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 133 CF₃ phenyl N-methylimidazol-2-yl 134 CF₃ phenyl 4-methylimidazol-5-yl 135 CF₃ phenyl 5-CF₃-pyrazol-1-yl 136 CF₃ 2-F-phenyl N-methylimidazol-2-yl 137 CF₃ 2-F-phenyl 4-methylimidazol-5-yl 138 CF₃ 2-F-phenyl 5-CF₃-pyrazol-1-yl 139 CF₃ phenyl guanidino 140 CF₃ phenyl 2-thiazolin-2-ylamine 141 CF₃ phenyl N-methyl-2-imidazolin-2-yl 142 CF₃ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 143 CF₃ phenyl N-methylimidazol-2-ylthiol 144 CF₃ phenyl t-butoxycarbonylamine 145 CF₃ phenyl (N-pyrrolidino)formylimino 146 CF₃ phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 147 CF₃ 2-F-phenyl guanidino 148 CF₃ 2-F-phenyl 2-thiazolin-2-ylamine 149 CF₃ 2-F-phenyl N-methyl-2-imidazolin-2-yl 150 CF₃ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 151 CF₃ 2-F-phenyl N-methylimidazol-2-ylthio 152 CF₃ 2-F-phenyl t-butoxycarbonylamine 153 CF₃ 2-F-phenyl (N-pyrrolidino)formylimino 154 CF₃ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 155 CF₃ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 156 CF₃ 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 157 CONH₂ phenyl 2-((Me)₂N-methyl)phenyl 158 CONH₂ phenyl 2-((Me)NH-methyl)phenyl 159 CONH₂ phenyl 2-(H₂N-methyl)phenyl 160 CONH₂ phenyl 2-HOCH₂-phenyl 161 CONH₂ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 162 CONH₂ 2-F-phenyl 2-((Me)NH-methyl)phenyl 163 CONH₂ 2-F-phenyl 2-(H₂N-methyl)phenyl 164 CONH₂ 2-F-phenyl 2-HOCH₂-phenyl 165 CONH₂ phenyl 2-methylimidazol-1-yl 166 CONH₂ phenyl 2-ethylimidazol-1-yl 167 CONH₂ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 168 CONH₂ phenyl 2-CH₃SO₂-imidazol-1-yl 169 CONH₂ phenyl 2-CH₃OCH₂-imidazol-1-yl 170 CONH₂ 2-F-phenyl 2-methylimidazol-1-yl 171 CONH₂ 2-F-phenyl 2-ethylimidazol-1-yl 172 CONH₂ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 173 CONH₂ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 174 CONH₂ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 175 CONH₂ 2-Cl-phenyl 2-methylimidazol-1-yl 176 CONH₂ 2-Cl-phenyl 2-ethylimidazol-1-yl 177 CONH₂ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 178 CONH₂ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 179 CONH₂ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 180 CONH₂ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 181 CONH₂ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 182 CONH₂ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 183 CONH₂ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 184 CONH₂ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 185 CONH₂ phenyl N-methylimidazol-2-yl 186 CONH₂ phenyl 4-methylimidazol-5-yl 187 CONH₂ phenyl 5-CF₃-pyrazol-1-yl 188 CONH₂ 2-F-phenyl N-methylimidazol-2-yl 189 CONH₂ 2-F-phenyl 4-methylimidazol-5-yl 190 CONH₂ 2-F-phenyl 5-CF₃-pyrazol-1-yl 191 CONH₂ phenyl guanidino 192 CONH₂ phenyl 2-thiazolin-2-ylamine 193 CONH₂ phenyl N-methyl-2-imidazolin-2-yl 194 CONH₂ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 195 CONH₂ phenyl N-methylimidazol-2-ylthiol 196 CONH₂ phenyl t-butoxycarbonylamine 197 CONH₂ phenyl (N-pyrrolidino)formylimino 198 CONH₂ phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 199 CONH₂ 2-F-phenyl guanidino 200 CONH₂ 2-F-phenyl 2-thiazolin-2-ylamine 201 CONH₂ 2-F-phenyl N-methyl-2-imidazolin-2-yl 202 CONH₂ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 203 CONH₂ 2-F-phenyl N-methylimidazol-2-ylthio 204 CONH₂ 2-F-phenyl t-butoxycarbdnylamine 205 CONH₂ 2-F-phenyl (N-pyrrolidino)formylimino 206 CONH₂ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 207 CONH₂ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 208 CONH₂ 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 209 SCH₃ phenyl 2-((Me)₂N-methyl)phenyl 210 SCH₃ phenyl 2-((Me)NH-methyl)phenyl 211 SCH₃ phenyl 2-(H₂N-methyl)phenyl 212 SCH₃ phenyl 2-HOCH₂-phenyl 213 SCH₃ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 214 SCH₃ 2-F-phenyl 2-((Me)NH-methyl)phenyl 215 SCH₃ 2-F-phenyl 2-(H₂N-methyl)phenyl 216 SCH₃ 2-F-phenyl 2-HOCH₂-phenyl 217 SCH₃ phenyl 2-methylimidazol-1-yl 218 SCH₃ phenyl 2-ethylimidazol-1-yl 219 SCH₃ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 220 SCH₃ phenyl 2-CH₃SO₂-imidazol-1-yl 221 SCH₃ phenyl 2-CH₃OCH₂-imidazol-1-yl 222 SCH₃ 2-F-phenyl 2-methylimidazol-1-yl 223 SCH₃ 2-F-phenyl 2-ethylimidazol-1-yl 224 SCH₃ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 225 SCH₃ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 226 SCH₃ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 227 SCH₃ 2-Cl-phenyl 2-methylimidazol-1-yl 228 SCH₃ 2-Cl-phenyl 2-ethylimidazol-1-yl 229 SCH₃ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 230 SCH₃ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 231 SCH₃ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 232 SCH₃ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 233 SCH₃ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 234 SCH₃ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 235 SCH₃ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 236 SCH₃ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 237 SCH₃ phenyl N-methylimidazol-2-yl 238 SCH₃ phenyl 4-methylimidazol-5-yl 239 SCH₃ phenyl 5-CF₃-pyrazol-1-yl 240 SCH₃ 2-F-phenyl N-methylimidazol-2-yl 241 SCH₃ 2-F-phenyl 4-methylimidazol-5-yl 242 SCH₃ 2-F-phenyl 5-CF₃-pyrazol-1-yl 243 SCH₃ phenyl guanidino 244 SCH₃ phenyl 2-thiazolin-2-ylamine 245 SCH₃ phenyl N-methyl-2-imidazolin-2-yl 246 SCH₃ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 247 SCH₃ phenyl N-methylimidazol-2-ylthiol 248 SCH₃ phenyl t-butoxycarbonylamine 249 SCH₃ phenyl (N-pyrrolidino)formylimino 250 SCH₃ phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 251 SCH₃ 2-F-phenyl guanidino 252 SCH₃ 2-F-phenyl 2-thiazolin-2-ylamine 253 SCH₃ 2-F-phenyl N-methyl-2-imidazolin-2-yl 254 SCH₃ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 255 SCH₃ 2-F-phenyl N-methylimidazol-2-ylthio 256 SCH₃ 2-F-phenyl t-butoxycarbonylamine 257 SCH₃ 2-F-phenyl (N-pyrrolidino)formylimino 258 SCH₃ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 259 SCH₃ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 260 SCH₃ 2-CH₃O-phenyl (N-pyrrclidino)formyl-N-(methanesulfamoyl)imino 261 SO₂CH₃ phenyl 2-((Me)₂N-methyl)phenyl 262 SO₂CH₃ phenyl 2-((Me)NH-methyl)phenyl 263 SO₂CH₃ phenyl 2-(H₂N-methyl)phenyl 264 SO₂CH₃ phenyl 2-HOCH₂-phenyl 265 SO₂CH₃ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 266 SO₂CH₃ 2-F-phenyl 2-((Me)NH-methyl)phenyl 267 SO₂CH₃ 2-F-phenyl 2-(H₂N-methyl)phenyl 268 SO₂CH₃ 2-F-phenyl 2-HOCH₂-phenyl 269 SO₂CH₃ phenyl 2-methylimidazol-1-yl 270 SO₂CH₃ phenyl 2-ethylimidazol-1-yl 271 SO₂CH₃ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 272 SO₂CH₃ phenyl 2-CH₃SO₂-imidazol-1-yl 273 SO₂CH₃ phenyl 2-CH₃OCH₂-imidazol-1-yl 274 SO₂CH₃ 2-F-phenyl 2-methylimidazol-1-yl 275 SO₂CH₃ 2-F-phenyl 2-ethylimidazol-1-yl 276 SO₂CH₃ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 277 SO₂CH₃ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 278 SO₂CH₃ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 279 SO₂CH₃ 2-Cl-phenyl 2-methylimidazol-1-yl 280 SO₂CH₃ 2-Cl-phenyl 2-ethylimidazol-1-yl 281 SO₂CH₃ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 282 SO₂CH₃ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 283 SO₂CH₃ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 284 SO₂CH₃ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 285 SO₂CH₃ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 286 SO₂CH₃ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 287 SO₂CH₃ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 288 SO₂CH₃ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 289 SO₂CH₃ phenyl N-methylimidazol-2-yl 290 SO₂CH₃ phenyl 4-methylimidazol-5-yl 291 SO₂CH₃ phenyl 5-CF₃-pyrazol-1-yl 292 SO₂CH₃ 2-F-phenyl N-methylimidazol-2-yl 293 SO₂CH₃ 2-F-phenyl 4-methylimidazol-5-yl 294 SO₂CH₃ 2-F-phenyl 5-CF₃-pyrazol-1-yl 295 SO₂CH₃ phenyl guanidino 296 SO₂CH₃ phenyl 2-thiazolin-2-ylamine 297 SO₂CH₃ phenyl N-methyl-2-imidazolin-2-yl 298 SO₂CH₃ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 299 SO₂CH₃ phenyl N-methylimidazol-2-ylthiol 300 SO₂CH₃ phenyl t-butoxycarbonylamine 301 SO₂CH₃ phenyl (N-pyrrolidino)formylimino 302 SO₂CH₃ phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 303 SO₂CH₃ 2-F-phenyl guanidino 304 SO₂CH₃ 2-F-phenyl 2-thiazolin-2-ylamine 305 SO₂CH₃ 2-F-phenyl N-methyl-2-imidazolin-2-yl 306 SO₂CH₃ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 307 SO₂CH₃ 2-F-phenyl N-methylimidazol-2-ylthio 308 SO₂CH₃ 2-F-phenyl t-butoxycarbonylamine 309 SO₂CH₃ 2-F-phenyl (N-pyrrolidino)formylimino 310 SO₂CH₃ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 311 SO₂CH₃ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 312 SO₂CH₃ 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 313 NHSO₂CH₃ phenyl 2-((Me)₂N-methyl)phenyl 314 NHSO₂CH₃ phenyl 2-((Me)NH-methyl)phenyl 315 NHSO₂CH₃ phenyl 2-(H₂N-methyl)phenyl 316 NHSO₂CH₃ phenyl 2-HOCH₂-phenyl 317 NHSO₂CH₃ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 318 NHSO₂CH₃ 2-F-phenyl 2-((Me)NH-methyl)phenyl 319 NHSO₂CH₃ 2-F-phenyl 2-(H₂N-methyl)phenyl 320 NHSO₂CH₃ 2-F-phenyl 2-HOCH₂-phenyl 321 NHSO₂CH₃ phenyl 2-methylimidazol-1-yl 322 NHSO₂CH₃ phenyl 2-ethylimidazol-1-yl 323 NHSO₂CH₃ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 324 NHSO₂CH₃ phenyl 2-CH₃SO₂-imidazol-1-yl 325 NHSO₂CH₃ phenyl 2-CH₃OCH₂-imidazol-1-yl 326 NHSO₂CH₃ 2-F-phenyl 2-methylimidazol-1-yl 327 NHSO₂CH₃ 2-F-phenyl 2-ethylimidazol-1-yl 328 NHSO₂CH₃ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 329 NHSO₂CH₃ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 330 NHSO₂CH₃ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 331 NHSO₂CH₃ 2-Cl-phenyl 2-methylimidazol-1-yl 332 NHSO₂CH₃ 2-Cl-phenyl 2-ethylimidazol-1-yl 333 NHSO₂CH₃ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 334 NHSO₂CH₃ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 335 NHSO₂CH₃ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 336 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 337 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 338 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 339 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 340 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 341 NHSO₂CH₃ phenyl N-methylimidazol-2-yl 342 NHSO₂CH₃ phenyl 4-methylimidazol-5-yl 343 NHSO₂CH₃ phenyl 5-CF₃-pyrazol-1-yl 344 NHSO₂CH₃ 2-F-phenyl N-methylimidazol-2-yl 345 NHSO₂CH₃ 2-F-phenyl 4-methylimidazol-5-yl 346 NHSO₂CH₃ 2-F-phenyl 5-CF₃-pyrazol-1-yl 347 NHSO₂CH₃ phenyl guanidino 348 NHSO₂CH₃ phenyl 2-thiazolin-2-ylamine 349 NHSO₂CH₃ phenyl N-methyl-2-imidazolin-2-yl 350 NHSO₂CH₃ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 351 NHSO₂CH₃ phenyl N-methylimidazol-2-ylthiol 352 NHSO₂CH₃ phenyl t-butoxycarbonylamine 353 NHSO₂CH₃ phenyl (N-pyrrolidino)formylimino 354 NHSO₂CH₃ phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 355 NHSO₂CH₃ 2-F-phenyl guanidino 356 NHSO₂CH₃ 2-F-phenyl 2-thiazolin-2-ylamine 357 NHSO₂CH₃ 2-F-phenyl N-methyl-2-imidazolin-2-yl 358 NHSO₂CH₃ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 359 NHSO₂CH₃ 2-F-phenyl N-methylimidazol-2-ylthio 360 NHSO₂CH₃ 2-F-phenyl t-butoxycarbonylamine 361 NHSO₂CH₃ 2-F-phenyl (N-pyrrolidino)formylimino 362 NHSO₂CH₃ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 363 NHSO₂CH₃ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 364 NHSO₂CH₃ 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino

TABLE 4

a₁ R = F, D = NH₂ b₁ R = F, D = NH₂ c₁ R = F, D = NH₂ a₂ R = H, D = NH₂ b₂ R = H, D = NH₂ c₂ R = H, D = NH₂ a₃ R = F, D = CH₂NH₂ b₃ R = F, D = CH₂NH₂ c₃ R = F, D = CH₂NH₂ a₄ R = H, D = CH₂NH₂ b₄ R = H, D = CH₂NH₂ c₄ R = H, D = CH₂NH₂ a₅ R = F, D = C(═NH)NH₂ b₅ R = F, D = C(═NH)NH₂ c₅ R = F, D = C(═NH)NH₂ a₆ R = H, D = C(═NH)NH₂ b₆ R = H, D = C(═NH)NH₂ c₆ R = H, D = C(═NH)NH₂ a₇ R = F, D = C(O)NH₂ b₇ R = F, D = C(O)NH₂ c₇ R = F, D = C(O)NH₂ a₈ R = H, D = C(O)NH₂ b₆ R = H, D = C(O)NH₂ c₈ R = H, D = C(O)NH₂

d₁ R = F, D = NH₂ e₁ R = F, D = NH₂ f₁ R = F, D = NH₂ d₂ R = H, D = NH₂ e₂ R = H, D = NH₂ f₂ R = H, D = NH₂ d₃ R = F, D = CH₂NH₂ e₃ R = F, D = CH₂NH₂ f₃ R = F, D = CH₂NH₂ d₄ R = H, D = CH₂NH₂ e₄ R = H, D = CH₂NH₂ f₄ R = H, D = CH₂NH₂ d₅ R = F, D = C(═NH)NH₂ e₅ R = F, D = C(═NH)NH₂ f₅ R = F, D = C(═NH)NH₂ d₆ R = H, D = C(═NH)NH₂ e₆ R = H, D = C(═NH)NH₂ f₆ R = H, D = C(═NH)NH₂ d₇ R = F, D = C(O)NH₂ e₇ R = F, D = C(O)NH₂ f₇ R = F, D = C(O)NH₂ d₆ R = H, D = C(O)NH₂ e₈ R = H, D = C(O)NH₂ f₈ R = H, D = C(O)NH₂

g₁ R = F, D = NH₂ h₁ R = F, D = NH₂ i₁ R = F, D = NH₂ g₂ R = H, D = NH₂ h₂ R = H, D = NH₂ i₂ R = H, D = NH₂ g₃ R = F, D = CH₂NH₂ h₃ R = F, D = CH₂NH₂ i₃ R = F, D = CH₂NH₂ g₄ R = H, D = CH₂NH₂ h₄ R = H, D = CH₂NH₂ i₄ R = H, D = CH₂NH₂ g₅ R = F, D = C(═NH)NH₂ h₅ R = F, D = C(═NH)NH₂ i₅ R = F, D = C(═NH)NH₂ g₆ R = H, D = C(═NH)NH₂ h₆ R = H, D = C(═NH)NH₂ i₆ R = H, D = C(═NH)NH₂ g₇ R = F, D = C(O)NH₂ h₇ R = F, D = C(O)NH₂ i₇ R = F, D = C(O)NH₂ g₈ R = H, D = C(O)NH₂ h₈ R = H, D = C(O)NH₂ i₈ R = H, D = C(O)NH₂

j₁ R = F, D = NH₂ k₁ R = F, D = NH₂ l₁ R = F, D = NH₂ j₂ R = H, D = NH₂ k₂ R = H, D = NH₂ l₂ R = H, D = NH₂ j₃ R = F, D = CH₂NH₂ k₃ R = F, D = CH₂NH₂ l₃ R = F, D = CH₂NH₂ j₄ R = H, D = CH₂NH₂ k₄ R = H, D = CH₂NH₂ l₄ R = H, D = CH₂NH₂ j₅ R = F, D = C(═NH)NH₂ k₅ R = F, D = C(═NH)NH₂ l₅ R = F, D = C(═NH)NH₂ j₆ R = H, D = C(═NH)NH₂ k₆ R = H, D = C(═NH)NH₂ l₆ R = H, D = C(═NH)NH₂ j₇ R = F, D = C(O)NH₂ k₇ R = F, D = C(O)NH₂ l₇ R = F, D = C(O)NH₂ j₈ R = H, D = C(O)NH₂ k₈ R = H, D = C(O)NH₂ l₈ R = H, D = C(O)NH₂

m₁ R = F, D = NH₂ n₁ R = F, D = NH₂ o₁ R = F, D = NH₂ m₂ R = H, D = NH₂ n₂ R = H, D = NH₂ o₂ R = H, D = NH₂ m₃ R = F, D = CH₂NH₂ n₃ R = F, D = CH₂NH₂ o₃ R = F, D = CH₂NH₂ m₄ R = H, D = CH₂NH₂ n₄ R = H, D = CH₂NH₂ o₄ R = H, D = CH₂NH₂ m₅ R = F, D = C(═NH)NH₂ n₅ R = F, D = C(═NH)NH₂ o₅ R = F, D = C(═NH)NH₂ m₆ R = H, D = C(═NH)NH₂ n₆ R = H, D = C(═NH)NH₂ o₆ R = H, D = C(═NH)NH₂ m₇ R = F, D = C(O)NH₂ n₇ R = F, D = C(O)NH₂ o₇ R = F, D = C(O)NH₂ m₈ R = H, D = C(O)NH₂ n₈ R = H, D = C(O)NH₂ o₈ R = H, D = C(O)NH₂

p₁ R = F, D = NH₂ q₁ R = F, D = NH₂ r₁ R = F, D = NH₂ p₂ R = Cl, D = NH₂ q₂ R = Cl, D = NH₂ r₂ R = Cl, D = NH₂ p₃ R = OMe, D = NH₂ q₃ R = OMe, D = NH₂ r₃ R = OMe, D = NH₂ p₄ R = F, D = CH₂NH₂ q₄ R = F, D = CH₂NH₂ r₄ R = F, D = CH₂NH₂ p₅ R = Cl, D = CH₂NH₂ q₅ R = Cl, D = CH₂NH₂ r₅ R = Cl, D = CH₂NH₂ p₆ R = OMe, D = CH₂NH₂ q₆ R = OMe, D = CH₂NH₂ r₆ R = OMe, D = CH₂NH₂ p₇ R = F, D = C(═NH)NH₂ q₇ R = F, D = C(═NH)NH₂ r₇ R = F, D = C(═NH)NH₂ p₈ R = Cl, D = C(═NH)NH₂ q₈ R = Cl, D = C(═NH)NH₂ r₈ R = Cl, D = C(═NH)NH₂ p₉ R = OMe, D = C(═NH)NH₂ q₉ R = OMe, D = C(═NH)NH₂ r₉ R = OMe, D = C(═NH)NH₂ p₁₀ R = F, D = C(O)NH₂ q₁₀ R = F, D = C(O)NH₂ r₁₀ R = F, D = C(O)NH₂ p₁₁ R = Cl, D = C(O)NH₂ q₁₁ R = Cl, D = C(O)NH₂ r₁₁ R = Cl, D = C(O)NH₂ p₁₂ R = OMe, D = C(O)NH₂ q₁₂ R = OMe, D = C(9)NH₂ r₁₂ R = OMe, D = C(O)NH₂

s₁ R = F, D = NH₂ t₁ R = F, D = NH₂ u₁ R = F, D = NH₂ s₂ R = Cl, D = NH₂ t₂ R = Cl, D = NH₂ u₂ R = Cl, D = NH₂ s₃ R = OMe, D = NH₂ t₃ R = OMe, D = NH₂ u₃ R = OMe, D = NH₂ s₄ R = F, D = CH₂NH₂ t₄ R = F, D = CH₂NH₂ u₄ R = F, D = CH₂NH₂ s₅ R = Cl, D = CH₂NH₂ t₅ R = Cl, D = CH₂NH₂ u₅ R = Cl, D = CH₂NH₂ s₆ R = OMe, D = CH₂NH₂ t₆ R = OMe, D = CH₂NH₂ u₆ R = OMe, D = CH₂NH₂ s₇ R = F, D = C(═NH)NH₂ t₇ R = F, D = C(═NH)NH₂ u₇ R = F, D = C(═NH)NH₂ s₈ R = Cl, D = C(═NH)NH₂ t₈ R = Cl, D = C(═NH)NH₂ u₈ R = Cl, D = C(═NH)NH₂ s₉ R = OMe, D = C(═NH)NH₂ t₉ R = OMe, D = C(═NH)NH₂ u₉ R = OMe, D = C(═NH)NH₂ s₁₀ R = F, D = C(O)NH₂ t₁₀ R = F, D = C(O)NH₂ u₁₀ R = F, D = C(O)NH₂ s₁₁ R = Cl, D = C(O)NH₂ t₁₁ R = Cl, D = C(O)NH₂ u₁₁ R = Cl, D = C(O)NH₂ s₁₂ R = OMe, D = C(O)NH₂ t₁₂ R = OMe, D = C(O)NH₂ u₁₂ R = OMe, D = C(O)NH₂

v₁ R = F, D = NH₂ w₁ R = F, D = NH₂ x₁ R = F, D = NH₂ v₂ R = Cl, D = NH₂ w₂ R = Cl, D = NH₂ x₂ R = Cl, D = NH₂ v₃ R = OMe, D = NH₂ w₃ R = OMe, D = NH₂ x₃ R = OMe, D = NH₂ v₄ R = F, D = CH₂NH₂ w₄ R = F, D = CH₂NH₂ x₄ R = F, D = CH₂NH₂ v₅ R = Cl, D = CH₂NH₂ w₅ R = Cl, D = CH₂NH₂ x₅ R = Cl, D = CH₂NH₂ v₆ R = OMe, D = CH₂NH₂ w₆ R = OMe, D = CH₂NH₂ x₆ R = OMe, D = CH₂NH₂ v₇ R = F, D = C(═NH)NH₂ w₇ R = F, D = C(═NH)NH₂ x₇ R = F, D = C(═NH)NH₂ v₈ R = Cl, D = C(═NH)NH₂ w₈ R = Cl, D = C(═NH)NH₂ x₈ R = Cl, D = C(═NH)NH₂ v₉ R = OMe, D = C(═NH)NH₂ w₉ R = OMe, D = C(═NH)NH₂ x₉ R = OMe, D = C(═NH)NH₂ v₁₀ R = F, D = C(O)NH₂ w₁₀ R = F, D = C(O)NH₂ x₁₀ R = F, D = C(O)NH₂ v₁₁ R = Cl, D = C(O)NH₂ w₁₁ R = Cl, D = C(O)NH₂ x₁₁ R = Cl, D = C(O)NH₂ v₁₂ R = OMe, D = C(O)NH₂ w₁₂ R = OMe, D = C(O)NH₂ x₁₂ R = OMe, D = C(O)NH₂

y₁ R = F, D = NH₂ z₁ R = F, D = NH₂ aa₁ R = F, D = NH₂ y₂ R = Cl, D = NH₂ z₂ R = Cl, D = NH₂ aa₂ R = Cl, D = NH₂ y₃ R = OMe, D = NH₂ z₃ R = OMe, D = NH₂ aa₃ R = OMe, D = NH₂ y₄ R = F, D = CH₂NH₂ z₄ R = F, D = CH₂NH₂ aa₄ R = F, D = CH₂NH₂ y₅ R = Cl, D = CH₂NH₂ z₅ R = Cl, D = CH₂NH₂ aa₅ R = Cl, D = CH₂NH₂ y₆ R = OMe, D = CH₂NH₂ z₆ R = OMe, D = CH₂NH₂ aa₆ R = OMe, D = CH₂NH₂ y₇ R = F, D = C(═NH)NH₂ z₇ R = F, D = C(═NH)NH₂ aa₇ R = F, D = C(═NH)NH₂ y₈ R = Cl, D = C(═NH)NH₂ z₈ R = Cl, D = C(═NH)NH₂ aa₈ R = Cl, D = C(═NH)NH₂ y₉ R = OMe, D = C(═NH)NH₂ z₉ R = OMe, D = C(═NH)NH₂ aa₉ R = OMe, D = C(═NH)NH₂ y₁₀ R = F, D = C(O)NH₂ z₁₀ R = F, D = C(O)NH₂ aa₁₀ R = F, D = C(O)NH₂ y₁₁ R = Cl, D = C(O)NH₂ z₁₁ R = Cl, D = C(O)NH₂ aa₁₁ R = Cl, D = C(O)NH₂ y₁₂ R = OMe, D = C(O)NH₂ z₁₂ R = OMe, D = C(O)NH₂ aa₁₂ R = OMe, D = C(O)NH₂

bb₁ R = F, D = NH₂ cc₁ R = F, D = NH₂ dd₁ R = F, D = NH₂ bb₂ R = Cl, D = NH₂ cc₂ R = Cl, D = NH₂ dd₂ R = Cl, D = NH₂ bb₃ R = OMe, D = NH₂ cc₃ R = OMe, D = NH₂ dd₃ R = OMe, D = NH₂ bb₄ R = F, D = CH₂NH₂ cc₄ R = F, D = CH₂NH₂ dd₄ R = F, D = CH₂NH₂ bb₅ R = Cl, D = CH₂NH₂ cc₅ R = Cl, D = CH₂NH₂ dd₅ R = Cl, D = CH₂NH₂ bb₆ R = OMe, D = CH₂NH₂ cc₆ R = OMe, D = CH₂NH₂ dd₆ R = OMe, D = CH₂NH₂ bb₇ R = F, D = C(═NH)NH₂ cc₇ R = F, D = C(═NH)NH₂ dd₇ R = F, D = C(═NH)NH₂ bb₈ R = Cl, D = C(═NH)NH₂ cc₈ R = Cl, D = C(═NH)NH₂ dd₈ R = Cl, D = C(═NH)NH₂ bb₉ R = OMe, D = C(═NH)NH₂ cc₉ R = OMe, D = C(═NH)NH₂ dd₉ R = OMe, D = C(═NH)NH₂ bb₁₀ R = F, D = C(O)NH₂ cc₁₀ R = F, D = C(O)NH₂ dd₁₀ R = F, D = C(O)NH₂ bb₁₁ R = Cl, D = C(O)NH₂ cc₁₁ R = Cl, D = C(O)NH₂ dd₁₁ R = Cl, D = C(O)NH₂ bb₁₂ R = OMe, D = C(O)NH₂ cc₁₂ R = OMe, D = C(O)NH₂ dd₁₂ R = OMe, D = C(O)NH₂

ee₁ R = F, D = CH₂NH₂ ff₁ R = F, D = CH₂NH₂ gg₁ R = F, D = CH₂NH₂ ee₂ R = Cl, D = CH₂NH₂ ff₂ R = Cl, D = CH₂NH₂ gg₂ R = Cl, D = CH₂NH₂ ee₃ R = OMe, D = CH₂NH₂ ff₃ R = OMe, D = CH₂NH₂ gg₃ R = OMe, D = CH₂NH₂ ee₄ R = CH₂NH₂, D = CH₂NH₂ ff₄ R = CH₂NH₂, D = CH₂NH₂ gg₄ R = CH₂NH₂, D = CH₂NH₂

hh₁ R = F, D = CH₂NH₂ ii₁ R = F, D = CH₂NH₂ jj₁ R = F, D = CH₂NH₂ hh₂ R = Cl, D = CH₂NH₂ ii₂ R = Cl, D = CH₂NH₂ jj₂ R = Cl, D = CH₂NH₂ hh₃ R = OMe, D = CH₂NH₂ ii₃ R = OMe, D = CH₂NH₂ jj₃ R = OMe, D = CH₂NH₂ hh₄ R = CH₂NH₂, D = CH₂NH₂ ii₄ R = CH₂NH₂, D = CH₂NH₂ jj₄ R = CH₂NH₂, D = CH₂NH₂

kk₁ R = F, D = CH₂NH₂ ll₁ R = F, D = CH₂NH₂ mm₁ R = F, D = CH₂NH₂ kk₂ R = Cl, D = CH₂NH₂ ll₂ R = Cl, D = CH₂NH₂ mm₂ R = Cl, D = CH₂NH₂ kk₃ R = OMe, D = CH₂NH₂ ll₃ R = OMe, D = CH₂NH₂ mm₃ R = OMe, D = CH₂NH₂ kk₄ R = CH₂NH₂, D = CH₂NH₂ ll₄ R = CH₂NH₂, D = CH₂NH₂ mm₄ R = CH₂NH₂, D = CH₂NH₂

nn₁ R = F, D = CH₂NH₂ oo₁ R = F, D = CH₂NH₂ pp₁ R = F, D = CH₂NH₂ nn₂ R = Cl, D = CH₂NH₂ oo₂ R = Cl, D = CH₂NH₂ pp₂ R = Cl, D = CH₂NH₂ nn₃ R = OMe, D = CH₂NH₂ oo₃ R = OMe, D = CH₂NH₂ pp₃ R = OMe, D = CH₂NH₂ nn₄ R = CH₂NH₂, D = CH₂NH₂ oo₄ R = CH₂NH₂, D = CH₂NH₂ pp₄ R = CH₂NH₂, D = CH₂NH₂

qq₁ R = F, D = CH₂NH₂ rr₁ R = F, D = CH₂NH₂ ss₁ R = F, D = CH₂NH₂ qq₂ R = Cl, D = CH₂NH₂ rr₂ R = Cl, D = CH₂NH₂ ss₂ R = Cl, D = CH₂NH₂ qq₃ R = OMe, D = CH₂NH₂ rr₃ R = OMe, D = CH₂NH₂ ss₃ R = OMe, D = CH₂NH₂ qq₄ R = CH₂NH₂, D = CH₂NH₂ rr₄ R = CH₂NH₂, D = CH₂NH₂ ss₄ R = CH₂NH₂, D = CH₂NH₂ Ex. # R^(1b) A B  1 H phenyl 2-(aminosulfonyl)phenyl  2 H phenyl 2-(methylaminosulfonyl)phenyl  3 H phenyl 1-pyrrolidinocarbonyl  4 H phenyl 2-(methylsulfonyl)phenyl  5 H phenyl 4-morpholino  6 H phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  7 H phenyl 4-morpholinocarbonyl  8 H 2-pyridyl 2-(aminosulfonyl)phenyl  9 H 2-pyridyl 2-(methylaminosulfonyl)phenyl  10 H 2-pyridyl 1-pyrrolidinocarbonyl  11 H 2-pyridyl 2-(methylsulfonyl)phenyl  12 H 2-pyridyl 4-morpholino  13 H 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  14 H 2-pyridyl 4-morpholinocarbonyl  15 H 3-pyridyl 2-(aminosulfonyl)phenyl  16 H 3-pyridyl 2-(methylaminosulfonyl)phenyl  17 H 3-pyridyl 1-pyrrolidinocarbonyl  18 H 3-pyridyl 2-(methylsulfonyl)phenyl  19 H 3-pyridyl 4-morpholino  20 H 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  21 H 3-pyridyl 4-morpholinocarbonyl  22 H 2-pyrimidyl 2-(aminosulfonyl)phenyl  23 H 2-pyrimidyl 2-(methylaminosulfonyl)phenyl  24 H 2-pyrimidyl 1-pyrrolidinocarbonyl  25 H 2-pyrimidyl 2-(methylsulfonyl)phenyl  26 H 2-pyrimidyl 4-morpholino  27 H 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  28 H 2-pyrimidyl 4-morpholinocarbonyl  29 H 5-pyrimidyl 2-(aminosulfonyl)phenyl  30 H 5-pyrimidyl 2-(methylaminosulfonyl)phenyl  31 H 5-pyrimidyl 1-pyrrolidinocarbonyl  32 H 5-pyrimidyl 2-(methylsulfonyl)phenyl  33 H 5-pyrimidyl 4-morpholino  34 H 5-pyrimidyl 2-(1-CF₃-tetrazol-2-yl)phenyl  35 H 5-pyrimidyl 4-morpholinocarbonyl  36 H 2-Cl-phenyl 2-(aminosulfonyl)phenyl  37 H 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl  38 H 2-Cl-phenyl 1-pyrrolidinocarbonyl  39 H 2-Cl-phenyl 2-(methylsulfonyl)phenyl  40 H 2-Cl-phenyl 4-morpholino  41 H 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  42 H 2-Cl-phenyl 4-morpholinocarbonyl  43 H 2-F-phenyl 2-(aminosulfonyl)phenyl  44 H 2-F-phenyl 2-(methylaminosulfonyl)phenyl  45 H 2-F-phenyl 1-pyrrolidinocarbonyl  46 H 2-F-phenyl 2-(methylsulfonyl)phenyl  47 H 2-F-phenyl 4-morpholino  48 H 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  49 H 2-F-phenyl 4-morpholinocarbonyl  50 H 2,5-diF-phenyl 2-(aminosulfonyl)phenyl  51 H 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl  52 H 2,5-diF-phenyl 1-pyrrolidinocarbonyl  53 H 2,5-diF-phenyl 2-(methylsulfonyl)phenyl  54 H 2,5-diF-phenyl 4-morpholino  55 H 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  56 H 2,5-diF-phenyl 4-morpholinocarbonyl  57 H phenyl 2-(aminosulfonyl)phenyl  58 —CN phenyl 2-(methylaminosulfonyl)phenyl  59 —CN phenyl 1-pyrrolidinocarbonyl  60 —CN phenyl 2-(methylsulfonyl)phenyl  61 —CN phenyl 4-morpholino  62 —CN phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  63 —CN phenyl 4-morpholinocarbonyl  64 —CN 2-pyridyl 2-(aminosulfonyl)phenyl  65 —CN 2-pyridyl 2-(methylaminosulfonyl)phenyl  66 —CN 2-pyridyl 1-pyrrolidinocarbonyl  67 —CN 2-pyridyl 2-(methylsulfonyl)phenyl  68 —CN 2-pyridyl 4-morpholino  69 —CN 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  70 —CN 2-pyridyl 4-morpholinocarbonyl  71 —CN 3-pyridyl 2-(aminosulfonyl)phenyl  72 —CN 3-pyridyl 2-(methylaminosulfonyl)phenyl  73 —CN 3-pyridyl 1-pyrrolidinocarbonyl  74 —CN 3-pyridyl 2-(methylsulfonyl)phenyl  75 —CN 3-pyridyl 4-morpholino  76 —CN 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  77 —CN 3-pyridyl 4-morpholinocarbonyl  78 —CN 2-pyrimidyl 2-(aminosulfonyl)phenyl  79 —CN 2-pyrimidyl 2-(methylaminosulfonyl)phenyl  80 —CN 2-pyrimidyl 1-pyrrolidinocarbonyl  81 —CN 2-pyrimidyl 2-(methylsulfonyl)phenyl  82 —CN 2-pyrimidyl 4-morpholino  83 —CN 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  84 —CN 2-pyrimidyl 4-morpholinocarbonyl  85 —CN 5-pyrimidyl 2-(aminosulfonyl)phenyl  86 —CN 5-pyrimidyl 2-(methylaminosulfonyl)phenyl  87 —CN 5-pyrimidyl 1-pyrrolidinocarbonyl  88 —CN 5-pyrimidyl 2-(methylsulfonyl)phenyl  89 —CN 5-pyrimidyl 4-morpholino  90 —CN 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  91 —CN 5-pyrimidyl 4-morpholinocarbonyl  92 —CN 2-Cl-phenyl 2-(aminosulfonyl)phenyl  93 —CN 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl  94 —CN 2-Cl-phenyl 1-pyrrolidinocarbonyl  95 —CN 2-Cl-phenyl 2-(methylsulfonyl)phenyl  96 —CN 2-Cl-phenyl 4-morpholino  97 —CN 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl  98 —CN 2-Cl-phenyl 4-morpholinocarbonyl  99 —CN 2-F-phenyl 2-(aminosulfonyl)phenyl 100 —CN 2-F-phenyl 2-(methylaminosulfonyl)phenyl 101 —CN 2-F-phenyl 1-pyrrolidinocarbonyl 102 —CN 2-F-phenyl 2-(methylsulfonyl)phenyl 103 —CN 2-F-phenyl 4-morpholino 104 —CN 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 105 —CN 2-F-phenyl 4-morpholinocarbonyl 106 —CN 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 107 —CN 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyll 108 —CN 2,5-diF-phenyl 1-pyrrolidinocarbonyl 109 —CN 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 110 —CN 2,5-diF-phenyl 4-morpholino 111 —CN 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 112 —CN 2,5-diF-phenyl 4-morpholinocarbonyl 113 CF₃ phenyl 2-(aminosulfonyl)phenyl 114 CF₃ phenyl 2-(methylaminosulfonyl)phenyl 115 CF₃ phenyl 1-pyrrolidinocarbonyl 116 CF₃ phenyl 2-(methylsulfonyl)phenyl 117 CF₃ phenyl 4-morpholino 118 CF₃ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 119 CF₃ phenyl 4-morpholinocarbonyl 120 CF₃ 2-pyridyl 2-(aminosulfonyl)phenyl 121 CF₃ 2-pyridyl 2-(methylaininosulfonyl)phenyl 122 CF₃ 2-pyridyl 1-pyrrolidinocarbonyl 123 CF₃ 2-pyridyl 2-(methylsulfonyl)phenyl 124 CF₃ 2-pyridyl 4-morpholino 125 CF₃ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 126 CF₃ 2-pyridyl 4-morpholinocarbonyl 127 CF₃ 3-pyridyl 2-(aminosulfonyl)phenyl 128 CF₃ 3-pyridyl 2-(methylaminosulfonyl)phenyl 129 CF₃ 3-pyridyl 1-pyrrolidinocarbonyl 130 CF₃ 3-pyridyl 2-(methylsulfonyl)phenyl 131 CF₃ 3-pyridyl 4-morpholino 132 CF₃ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 133 CF₃ 3-pyridyl 4-morpholinocarbonyl 134 CF₃ 2-pyrimidyl 2-(aminosulfonyl)phenyl 135 CF₃ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 136 CF₃ 2-pyrimidyl 1-pyrrolidinocarbonyl 137 CF₃ 2-pyrimidyl 2-(methylsulfonyl)phenyl 138 CF₃ 2-pyrimidyl 4-morpholino 139 CF₃ 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 140 CF₃ 2-pyrimidyl 4-morpholinocarbonyl 141 CF₃ 5-pyrimidyl 2-(aminosulfonyl)phenyl 142 CF₃ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 143 CF₃ 5-pyrimidyl 1-pyrrolidinocarbonyl 144 CF₃ 5-pyrimidyl 2-(methylsulfonyl)phenyl 145 CF₃ 5-pyrimidyl 4-morpholino 146 CF₃ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 147 CF₃ 5-pyrimidyl 4-morpholinocarbonyl 148 CF₃ 2-Cl-phenyl 2-(aminosulfonyl)phenyl 149 CF₃ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 150 CF₃ 2-Cl-phenyl 1-pyrrolidinocarbonyl 151 CF₃ 2-Cl-phenyl 2-(methylsulfonyl)phenyl 152 CF₃ 2-Cl-phenyl 4-morpholino 153 CF₃ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 154 CF₃ 2-Cl-phenyl 4-morpholinocarbonyl 155 CF₃ 2-F-phenyl 2-(aminosulfonyl)phenyl 156 CF₃ 2-F-phenyl 2-(methylaminosulfonyl)phenyl 157 CF₃ 2-F-phenyl 1-pyrrolidinocarbonyl 158 CF₃ 2-F-phenyl 2-(methylsulfonyl)phenyl 159 CF₃ 2-F-phenyl 4-morpholino 160 CF₃ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 161 CF₃ 2-F-phenyl 4-morpholinocarbonyl 162 CF₃ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 163 CF₃ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 164 CF₃ 2,5-diF-phenyl 1-pyrrolidinocarbonyl 165 CF₃ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 166 CF₃ 2,5-diF-phenyl 4-morpholino 167 CF₃ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 168 CF₃ 2,5-diF-phenyl 4-morpholinocarbonyl 169 CONH₂ phenyl 2-(aminosulfonyl)phenyl 170 CONH₂ phenyl 2-(methylaminosulfonyl)phenyl 171 CONH₂ phenyl 1-pyrrolidinocarbonyl 172 CONH₂ phenyl 2-(methylsulfonyl)phenyl 173 CONH₂ phenyl 4-morpholino 174 CONH₂ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 175 CONH₂ phenyl 4-morpholinocarbonyl 176 CONH₂ 2-pyridyl 2-(aminosuifonyl)phenyl 177 CONH₂ 2-pyridyl 2-(methylaminosulfonyl)phenyl 178 CONH₂ 2-pyridyl 1-pyrrolidinocarbonyl 179 CONH₂ 2-pyridyl 2-(methylsulfonyl)phenyl 180 CONH₂ 2-pyridyl 4-morpholino 181 CONH₂ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 182 CONH₂ 2-pyridyl 4-morpholinocarbonyl 183 CONH₂ 3-pyridyl 2-(aminosulfonyl)phenyl 184 CONH₂ 3-pyridyl 2-(methylaminosulfonyl)phenyl 185 CONH₂ 3-pyridyl 1-pyrrolidinocarbonyl 186 CONH₂ 3-pyridyl 2-(methylsulfonyl)phenyl 187 CONH₂ 3-pyridyl 4-morpholino 188 CONH₂ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 189 CONH₂ 3-pyridyl 4-morpholinocarbonyl 190 CONH₂ 2-pyrimidyl 2-(aminosulfonyl)phenyl 191 CONH₂ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 192 CONH₂ 2-pyrimidyl 1-pyrrolidinocarbonyl 193 CONH₂ 2-pyrimidyl 2-(methylsulfonyl)phenyL 194 CONH₂ 2-pyrimidyl 4-morpholino 195 CONH₂ 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 196 CONH₂ 2-pyrimidyl 4-morpholinocarbonyl 197 CONH₂ 5-pyrimidyl 2-(aminosulfonyl)phenyl 198 CONH₂ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 199 CONH₂ 5-pyrimidyl 1-pyrrolidinocarbonyl 200 CONH₂ 5-pyrimidyl 2-(methylsulfonyl)phenyl 201 CONH₂ 5-pyrimidyl 4-morpholino 202 CONH₂ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 203 CONH₂ 5-pyrimidyl 4-morpholinocarbonyl 204 CONH₂ 2-Cl-phenyl 2-(aminosulfonyl)phenyl 205 CONH₂ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 206 CONH₂ 2-Cl-phenyl 1-pyrrolidinocarbonyl 207 CONH₂ 2-Cl-phenyl 2-(methylsulfonyl)phenyl 208 CONH₂ 2-Cl-phenyl 4-morpholino 209 CONH₂ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 210 CONH₂ 2-Cl-phenyl 4-morpholinocarbonyl 211 CONH₂ 2-F-phenyl 2-(aminosulfonyl)phenyl 212 CONH₂ 2-F-phenyl 2-(methylaminosulfonyl)phenyl 213 CONH₂ 2-F-phenyl 1-pyrrolidinocarbonyl 214 CONH₂ 2-F-phenyl 2-(methylsulfonyl)phenyl 215 CONH₂ 2-F-phenyl 4-morpholino 216 CONH₂ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 217 CONH₂ 2-F-phenyl 4-morpholinocarbonyl 218 CONH₂ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 219 CONH₂ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 220 CONH₂ 2,5-diF-phenyl 1-pyrrolidinocarbonyl 221 CONH₂ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 222 CONH₂ 2,5-diF-phenyl 4-morpholino 223 CONH₂ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 224 CONH₂ 2,5-diF-phenyl 4-morpholinocarbonyl 225 SCH₃ phenyl 2-(aminosulfonyl)phenyl 226 SCH₃ phenyl 2-(methylaminosulfonyl)phenyl 227 SCH₃ phenyl 1-pyrrolidinocarbonyl 228 SCH₃ phenyl 2-(methylsulfonyl)phenyl 229 SCH₃ phenyl 4-morpholino 230 SCH₃ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 231 SCH₃ phenyl 4-morpholinocarbonyl 232 SCH₃ 2-pyridyl 2-(aminosulfonyl)phenyl 233 SCH₃ 2-pyridyl 2-(methylaminosulfonyl)phenyl 234 SCH₃ 2-pyridyl 1-pyrrolidinocarbonyl 235 SCH₃ 2-pyridyl 2-(methylsulfonyl)phenyl 236 SCH₃ 2-pyridyl 4-morpholino 237 SCH₃ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 238 SCH₃ 2-pyridyl 4-morpholinocarbonyl 239 SCH₃ 3-pyridyl 2-(aminosulfonyl)phenyl 240 SCH₃ 3-pyridyl 2-(methylaminosulfonyl)phenyl 241 SCH₃ 3-pyridyl 1-pyrrolidinocarbonyl 242 SCH₃ 3-pyridyl 2-(methylsulfonyl)phenyl 243 SCH₃ 3-pyridyl 4-morpholino 244 SCH₃ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 245 SCH₃ 3-pyridyl 4-morpholinocarbonyl 246 SCH₃ 2-pyrimidyl 2-(aminosulfonyl)phenyl 247 SCH₃ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 248 SCH₃ 2-pyrimidyl 1-pyrrolidinocarbonyl 249 SCH₃ 2-pyrimidyl 2-(methylsulfonyl)phenyl 250 SCH₃ 2-pyrimidyl 4-morpholino 251 SCH₃ 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 252 SCH₃ 2-pyrimidyl 4-morpholinocarbonyl 253 SCH₃ 5-pyrimidyl 2-(aminosulfonyl)phenyl 254 SCH₃ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 255 SCH₃ 5-pyrimidyl 1-pyrrolidinocarbonyl 256 SCH₃ 5-pyrimidyl 2-(methylsulfonyl)phenyl 257 SCH₃ 5-pyrimidyl 4-morpholino 258 SCH₃ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 259 SCH₃ 5-pyrimidyl 4-morpholinocarbonyl 260 SCH₃ 2-Cl-phenyl 2-(aminosulfonyl)phenyl 261 SCH₃ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 262 SCH₃ 2-Cl-phenyl 1-pyrrolidinocarbonyl 263 SCH₃ 2-Cl-phenyl 2-(methylsulfonyl)phenyl 264 SCH₃ 2-Cl-phenyl 4-morpholino 265 SCH₃ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 266 SCH₃ 2-Cl-phenyl 4-morpholinocarbonyl 267 SCH₃ 2-F-phenyl 2-(aminosulfonyl)phenyl 268 SCH₃ 2-F-phenyl 2-(methylaminosulfonyl)phenyl 269 SCH₃ 2-F-phenyl 1-pyrrolidinocarbonyl 270 SCH₃ 2-F-phenyl 2-(methylsulfonyl)phenyl 271 SCH₃ 2-F-phenyl 4-morpholino 272 SCH₃ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 273 SCH₃ 2-F-phenyl 4-morpholinocarbonyl 274 SCH₃ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 275 SCH₃ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 276 SCH₃ 2,5-diF-phenyl 1-pyrrolidinocarbonyl 277 SCH₃ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 278 SCH₃ 2,5-diF-phenyl 4-morpholino 279 SCH₃ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 280 SCH₃ 2,5-diF-phenyl 4-morpholinocarbonyl 281 SO₂CH₃ phenyl 2-(aminosulfonyl)phenyl 282 SO₂CH₃ phenyl 2-(methylaminosulfonyl)phenyl 283 SO₂CH₃ phenyl 1-pyrrolidinocarbonyl 284 SO₂CH₃ phenyl 2-(methylsulfonyl)phenyl 285 SO₂CH₃ phenyl 4-morpholino 286 SO₂CH₃ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 287 SO₂CH₃ phenyl 4-morpholinocarbonyl 288 SO₂CH₃ 2-pyridyl 2-(aminosulfonyl)phenyl 289 SO₂CH₃ 2-pyridyl 2-(methylaminosulfonyl)phenyl 290 SO₂CH₃ 2-pyridyl 1-pyrrolidinocarbonyl 291 SO₂CH₃ 2-pyridyl 2-(methylsulfonyl)phenyl 292 SO₂CH₃ 2-pyridyl 4-morpholino 293 SO₂CH₃ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 294 SO₂CH₃ 2-pyridyl 4-morpholinocarbonyl 295 SO₂CH₃ 3-pyridyl 2-(aminosulforiyl)phenyl 296 SO₂CH₃ 3-pyridyl 2-(methylaminosulfonyl)phenyl 297 SO₂CH₃ 3-pyridyl 1-pyrrolidinocarbonyL 298 SO₂CH₃ 3-pyridyl 2-(methylsulfonyl)phenyl 299 SO₂CH₃ 3-pyridyl 4-morpholino 300 SO₂CH₃ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 301 SO₂CH₃ 3-pyridyl 4-morpholinocarbonyl 302 SO₂CH₃ 2-pyrimidyl 2-(aminosulfonyl)phenyl 303 SO₂CH₃ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 304 SO₂CH₃ 2-pyrimidyl 1-pyrrolidinocarbonyl 305 SO₂CH₃ 2-pyrimidyl 2-(methylsulfonyl)phenyl 306 SO₂CH₃ 2-pyrimidyl 4-morpholino 307 SO₂CH₃ 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 308 SO₂CH₃ 2-pyrimidyl 4-morpholinocarbonyl 309 SO₂CH₃ 5-pyrimidyl 2-(aminosulfonyl)phenyl 310 SO₂CH₃ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 311 SO₂CH₃ 5-pyrimidyl 1-pyrrolidinocarbonyl 312 SO₂CH₃ 5-pyrimidyl 2-(methylsulfonyl)phenyl 313 SO₂CH₃ 5-pyrimidyl 4-morpholino 314 SO₂CH₃ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 315 SO₂CH₃ 5-pyrimidyl 4-morpholinocarbonyl 316 SO₂CH₃ 2-Cl-phenyl 2-(aminosulfonyl)phenyl 317 SO₂CH₃ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 318 SO₂CH₃ 2-Cl-phenyl 1-pyrrolidinocarbonyl 319 SO₂CH₃ 2-Cl-phenyl 2-(methylsulfonyl)phenyl 320 SO₂CH₃ 2-Cl-phenyl 4-morpholino 321 SO₂CH₃ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 322 SO₂CH₃ 2-Cl-phenyl 4-morpholinocarbonyl 323 SO₂CH₃ 2-F-phenyl 2-(aminosulfonyl)phenyl 324 SO₂CH₃ 2-F-phenyl 2-(methylaminosulfonyl)phenyl 325 SO₂CH₃ 2-F-phenyl 1-pyrrolidinocarbonyl 326 SO₂CH₃ 2-F-phenyl 2-(methylsulfonyl)phenyl 327 SO₂CH₃ 2-F-phenyl 4-morpholino 328 SO₂CH₃ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 329 SO₂CH₃ 2-F-phenyl 4-morpholinocarbonyl 330 SO₂CH₃ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 331 SO₂CH₃ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 332 SO₂CH₃ 2,5-diF-phenyl 1-pyrrolidinocarbonyl 333 SO₂CH₃ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 334 SO₂CH₃ 2,5-diF-phenyl 4-morpholino 335 SO₂CH₃ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 336 SO₂CH₃ 2,5-diF-phenyl 4-morpholinocarbonyl 337 NHSO₂CH₃ phenyl 2-(aminosulfonyl)phenyl 338 NHSO₂CH₃ phenyl 2-(methylaminosulfonyl)phenyl 339 NHSO₂CH₃ phenyl 1-pyrrolidinocarbonyl 340 NHSO₂CH₃ phenyl 2-(methylsulfonyl)phenyl 341 NHSO₂CH₃ phenyl 4-morpholino 342 NHSO₂CH₃ phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 343 NHSO₂CH₃ phenyl 4-morpholinocarbonyl 344 NHSO₂CH₃ 2-pyridyl 2-(aminosulfonyl)phenyl 345 NHSO₂CH₃ 2-pyridyl 2-(methylaminosulfonyl)phenyl 346 NHSO₂CH₃ 2-pyridyl 1-pyrrolidinocarbonyl 347 NHSO₂CH₃ 2-pyridyl 2-(methylsulfonyl)phenyl 348 NHSO₂CH₃ 2-pyridyl 4-morpholino 349 NHSO₂CH₃ 2-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 350 NHSO₂CH₃ 2-pyridyl 4-morpholinocarbonyl 351 NHSO₂CH₃ 3-pyridyl 2-(aminosulfonyl)phenyl 352 NHSO₂CH₃ 3-pyridyl 2-(methylaminosulfonyl)phenyl 353 NHSO₂CH₃ 3-pyridyl 1-pyrrolidinocarbonyl 354 NHSO₂CH₃ 3-pyridyl 2-(methylsulfonyl)phenyl 355 NHSO₂CH₃ 3-pyridyl 4-morpholino 356 NHSO₂CH₃ 3-pyridyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 357 NHSO₂CH₃ 3-pyridyl 4-morpholinocarbonyl 358 NHSO₂CH₃ 2-pyrimidyl 2-(aminosulfonyl)phenyl 359 NHSO₂CH₃ 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 360 NHSO₂CH₃ 2-pyrimidyl 1-pyrrolidinocarbonyl 361 NHSO₂CH₃ 2-pyrimidyl 2-(methylsulfonyl)phenyl 362 NHSO₂CH₃ 2-pyrimidyl 4-morpholino 363 NHSO₂CH₃ 2-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 364 NHSO₂CH₃ 2-pyrimidyl 4-morpholinocarbonyl 365 NHSO₂CH₃ 5-pyrimidyl 2-(aminosulfonyl)phenyl 366 NHSO₂CH₃ 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 367 NHSO₂CH₃ 5-pyrimidyl 1-pyrrolidinocarbonyl 368 NHSO₂CH₃ 5-pyrimidyl 2-(methylsulfonyl)phenyl 369 NHSO₂CH₃ 5-pyrimidyl 4-morpholino 370 NHSO₂CH₃ 5-pyrimidyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 371 NHSO₂CH₃ 5-pyrimidyl 4-morpholinocarbonyl 372 NHSO₂CH₃ 2-Cl-phenyl 2-(aminosulfonyl)phenyl 373 NHSO₂CH₃ 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 374 NHSO₂CH₃ 2-Cl-phenyl 1-pyrrolidinocarbonyl 375 NHSO₂CH₃ 2-Cl-phenyl 2-(methylsulfonyl)phenyl 376 NHSO₂CH₃ 2-Cl-phenyl 4-morpholino 377 NHSO₂CH₃ 2-Cl-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 378 NHSO₂CH₃ 2-Cl-phenyl 4-morpholinocarbonyl 379 NHSO₂CH₃ 2-F-phenyl 2-(aminosulfonyl)phenyl 380 NHSO₂CH₃ 2-F-phenyl 2-(methylaminosulfonyl)phenyl 381 NHSO₂CH₃ 2-F-phenyl 1-pyrrolidinocarbonyl 382 NHSO₂CH₃ 2-F-phenyl 2-(methylsulfonyl)phenyl 383 NHSO₂CH₃ 2-F-phenyl 4-morpholino 384 NHSO₂CH₃ 2-F-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 385 NHSO₂CH₃ 2-F-phenyl 4-morpholinocarbonyl 386 NHSO₂CH₃ 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 387 NHSO₂CH₃ 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 388 NHSO₂CH₃ 2,5-diF-phenyl 1-pyrrolidinocarbonyl 389 NHSO₂CH₃ 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 390 NHSO₂CH₃ 2,5-diF-phenyl 4-morpholino 391 NHSO₂CH₃ 2,5-diF-phenyl 2-(1′-CF₃-tetrazol-2-yl)phenyl 392 NHSO₂CH₃ 2,5-diF-phenyl 4-morpholinocarbonyl

TABLE 5

a₁ R = F, D = NH₂ b₁ R = F, D = NH₂ c₁ R = F, D = NH₂ a₂ R = H, D = NH₂ b₂ R = H, D = NH₂ c₂ R = H, D = NH₂ a₃ R = F, D = CH₂NH₂ b₃ R = F, D = CH₂NH₂ c₃ R = F, D = CH₂NH₂ a₄ R = H, D = CH₂NH₂ b₄ R = H, D = CH₂NH₂ c₄ R = H, D = CH₂NH₂ a₅ R = F, D = C(═NH)NH₂ b₅ R = F, D = C(═NH)NH₂ c₅ R = F, D = C(═NH)NH₂ a₆ R = H, D = C(═NH)NH₂ b₆ R = H, D = C(═NH)NH₂ c₆ R = H, D = C(═NH)NH₂ a₇ R = F, D = C(O)NH₂ b₇ R = F, D = C(O)NH₂ c₇ R = F, D = C(O)NH₂ a₈ R = H, D = C(O)NH₂ b₈ R = H, D = C(O)NH₂ c₈ R = H, D = C(O)NH₂

d₁ R = F, D = NH₂ e₁ R = F, D = NH₂ f₁ R = F, D = NH₂ d₂ R = H, D = NH₂ e₂ R = H, D = NH₂ f₂ R = H, D = NH₂ d₃ R = F, D = CH₂NH₂ e₃ R = F, D = CH₂NH₂ f₃ R = F, D = CH₂NH₂ d₄ R = H, D = CH₂NH₂ e₄ R = H, D = CH₂NH₂ f₄ R = H, D = CH₂NH₂ d₅ R = F, D = C(═NH)NH₂ e₅ R = F, D = C(═NH)NH₂ f₅ R = F, D = C(═NH)NH₂ d₆ R = H, D = C(═NH)NH₂ e₆ R = H, D = C(═NH)NH₂ f₆ R = H, D = C(═NH)NH₂ d₇ R = F, D = C(O)NH₂ e₇ R = F, D = C(O)NH₂ f₇ R = F, D = C(O)NH₂ d₈ R = H, D = C(O)NH₂ e₈ R = H, D = C(O)NH₂ f₈ R = H, D = C(O)NH₂

g₁ R = F, D = NH₂ h₁ R = F, D = NH₂ i₁ R = F, D = NH₂ g₂ R = H, D = NH₂ h₂ R = H, D = NH₂ i₂ R = H, D = NH₂ g₃ R = F, D = CH₂NH₂ h₃ R = F, D = CH₂NH₂ i₃ R = F, D = CH₂NH₂ g₄ R = H, D = CH₂NH₂ h₄ R = H, D = CH₂NH₂ i₄ R = H, D = CH₂NH₂ g₅ R = F, D = C(═NH)NH₂ h₅ R = F, D = C(═NH)NH₂ i₅ R = F, D = C(═NH)NH₂ g₆ R = H, D = C(═NH)NH₂ h₆ R = H, D = C(═NH)NH₂ i₆ R = H, D = C(═NH)NH₂ g₇ R = F, D = C(O)NH₂ h₇ R = F, D = C(O)NH₂ i₇ R = F, D = C(O)NH₂ g₈ R = H, D = C(O)NH₂ h₈ R = H, D = C(O)NH₂ i₈ R = H, D = C(O)NH₂

j₁ R = F, D = NH₂ k₁ R = F, D = NH₂ l₁ R = F, D = NH₂ j₂ R = H, D = NH₂ k₂ R = H, D = NH₂ l₂ R = H, D = NH₂ j₃ R = F, D = CH₂NH₂ k₃ R = F, D = CH₂NH₂ l₃ R = F, D = CH₂NH₂ j₄ R = H, D = CH₂NH₂ k₄ R = H, D = CH₂NH₂ l₄ R = H, D = CH₂NH₂ j₅ R = F, D = C(═NH)NH₂ k₅ R = F, D = C(═NH)NH₂ l₅ R = F, D = C(═NH)NH₂ j₆ R = H, D = C(═NH)NH₂ k₆ R = H, D = C(═NH)NH₂ l₆ R = H, D = C(═NH)NH₂ j₇ R = F, D = C(O)NH₂ k₇ R = F, D = C(O)NH₂ l₇ R = F, D = C(O)NH₂ j₈ R = H, D = C(O)NH₂ k₈ R = H, D = C(O)NH₂ l₈ R = H, D = C(O)NH₂

m₁ R = F, D = NH₂ n₁ R = F, D = NH₂ o₁ R = F, D = NH₂ m₂ R = H, D = NH₂ n₂ R = H, D = NH₂ o₂ R = H, D = NH₂ m₃ R = F, D = CH₂NH₂ n₃ R = F, D = CH₂NH₂ o₃ R = F, D = CH₂NH₂ m₄ R = H, D = CH₂NH₂ n₄ R = H, D = CH₂NH₂ o₄ R = H, D = CH₂NH₂ m₅ R = F, D = C(═NH)NH₂ n₅ R = F, D = C(═NH)NH₂ o₅ R = F, D = C(═NH)NH₂ m₆ R = H, D = C(═NH)NH₂ n₅ R = H, D = C(═NH)NH₂ o₆ R = H, D = C(═NH)NH₂ m₇ R = F, D = C(O)NH₂ n₇ R = F, D = C(O)NH₂ o₇ R = F, D = C(O)NH₂ m₈ R = H, D = C(O)NH₂ n₈ R = H, D = C(O)NH₂ o₈ R = H, D = C(O)NH₂

p₁ R = F, D = NH₂ q₁ R = F, D = NH₂ r₁ R = F, D = NH₂ p₂ R = Cl, D = NH₂ q₂ R = Cl, D = NH₂ r₂ R = Cl, D = NH₂ p₃ R = OMe, D = NH₂ q₃ R = OMe, D = NH₂ r₃ R = OMe, D = NH₂ p₄ R = F, D = CH₂NH₂ q₄ R = F, D = CH₂NH₂ r₄ R = F, D = CH₂NH₂ p₅ R = Cl, D = CH₂NH₂ q₅ R = Cl, D = CH₂NH₂ r₅ R = Cl, D = CH₂NH₂ p₆ R = OMe, D = CH₂NH₂ q₆ R = OMe, D = CH₂NH₂ r₆ R = OMe, D = CH₂NH₂ p₇ R = F, D = C(═NH)NH₂ q₇ R = F, D = C(═NH)NH₂ r₇ R = F, D = C(═NH)NH₂ p₈ R = Cl, D = C(═NH)NH₂ q₈ R = Cl, D = C(═NH)NH₂ r₈ R = Cl, D = C(═NH)NH₂ p₉ R = OMe, D = C(═NH)NH₂ q₉ R = OMe, D = C(═NH)NH₂ r₉ R = OMe, D = C(═NH)NH₂ p₁₀ R = F, D = C(O)NH₂ q₁₀ R = F, D = C(O)NH₂ r₁₀ R = F, D = C(O)NH₂ p₁₁ R = Cl, D = C(O)NH₂ q₁₁ R = Cl, D = C(O)NH₂ r₁₁ R = Cl, D = C(O)NH₂ p₁₂ R = OMe, D = C(O)NH₂ q₁₂ R = OMe, D = C(O)NH₂ r₁₂ R = OMe, D = C(O)NH₂

s₁ R = F, D = NH₂ t₁ R = F, D = NH₂ u₁ R = F, D = NH₂ s₂ R = Cl, D = NH₂ t₂ R = Cl, D = NH₂ u₂ R = Cl, D = NH₂ s₃ R = OMe, D = NH₂ t₃ R = OMe, D = NH₂ u₃ R = OMe, D = NH₂ s₄ R = F, D = CH₂NH₂ t₄ R = F, D = CH₂NH₂ u₄ R = F, D = CH₂NH₂ s₅ R = Cl, D = CH₂NH₂ t₅ R = Cl, D = CH₂NH₂ u₅ R = Cl, D = CH₂NH₂ s₆ R = OMe, D = CH₂NH₂ t₆ R = OMe, D = CH₂NH₂ u₆ R = OMe, D = CH₂NH₂ s₇ R = F, D = C(═NH)NH₂ t₇ R = F, D = C(═NH)NH₂ u₇ R = F, D = C(═NH)NH₂ s₈ R = Cl, D = C(═NH)NH₂ t₈ R = Cl, D = C(═NH)NH₂ u₈ R = Cl, D = C(═NH)NH₂ s₉ R = OMe, D = C(═NH)NH₂ t₉ R = OMe, D = C(═NH)NH₂ u₉ R = OMe, D = C(═NH)NH₂ s₁₀ R = F, D = C(O)NH₂ t₁₀ R = F, D = C(O)NH₂ u₁₀ R = F, D = C(O)NH₂ s₁₁ R = Cl, D = C(O)NH₂ t₁₁ R = Cl, D = C(O)NH₂ u₁₁ R = Cl, D = C(O)NH₂ s₁₂ R = OMe, D = C(O)NH₂ t₁₂ R = OMe, D = C(O)NH₂ u₁₂ R = OMe, D = C(O)NH₂

v₁ R = F, D = NH₂ w₁ R = F, D = NH₂ x₁ R = F, D = NH₂ v₂ R = Cl, D = NH₂ w₂ R = Cl, D = NH₂ x₂ R = Cl, D = NH₂ v₃ R = OMe, D = NH₂ w₃ R = OMe, D = NH₂ x₃ R = OMe, D = NH₂ v₄ R = F, D = CH₂NH₂ w₄ R = F, D = CH₂NH₂ x₄ R = F, D = CH₂NH₂ v₅ R = Cl, D = CH₂NH₂ w₅ R = Cl, D = CH₂NH₂ x₅ R = Cl, D = CH₂NH₂ v₆ R = OMe, D = CH₂NH₂ w₆ R = OMe, D = CH₂NH₂ x₆ R = OMe, D = CH₂NH₂ v₇ R = F, D = C(═NH)NH₂ w₇ R = F, D = C(═NH)NH₂ x₇ R = F, D = C(═NH)NH₂ v₈ R = Cl, D = C(═NH)NH₂ w₈ R = Cl, D = C(═NH)NH₂ x₆ R = Cl, D = C(═NH)NH₂ v₉ R = OMe, D = C(═NH)NH₂ w₉ R = OMe, D = C(═NH)NH₂ x₉ R = OMe, D = C(═NH)NH₂ v₁₀ R = F, D = C(O)NH₂ w₁₀ R = F, D = C(O)NH₂ x₁₀ R = F, D = C(O)NH₂ v₁₁ R = Cl, D = C(O)NH₂ w₁₁ R = Cl, D = C(O)NH₂ x₁₁ R = Cl, D = C(O)NH₂ v₁₂ R = OMe, D = C(O)NH₂ w₁₂ R = OMe, D = C(O)NH₂ x₁₂ R = OMe, D = C(O)NH₂

y₁ R = F, D = NH₂ z₁ R = F, D = NH₂ aa₁ R = F, D = NH₂ y₂ R = Cl, D = NH₂ z₂ R = Cl, D = NH₂ aa₂ R = Cl, D = NH₂ y₃ R = OMe, D = NH₂ z₃ R = OMe, D = NH₂ aa₃ R = OMe, D = NH₂ y₄ R = F, D = CH₂NH₂ z₄ R = F, D = CH₂NH₂ aa₄ R = F, D = CH₂NH₂ y₅ R = Cl, D = CH₂NH₂ z₅ R = Cl, D = CH₂NH₂ aa₅ R = Cl, D = CH₂NH₂ y₆ R = OMe, D = CH₂NH₂ z₆ R = OMe, D = CH₂NH₂ aa₆ R = OMe, D = CH₂NH₂ y₇ R = F, D = C(═NH)NH₂ z₇ R = F, D = C(═NH)NH₂ aa₇ R = F, D = C(═NH)NH₂ y₈ R = Cl, D = C(═NH)NH₂ z₈ R = Cl, D = C(═NH)NH₂ aa₈ R = Cl, D = C(═NH)NH₂ y₉ R = OMe, D = C(═NH)NH₂ z₉ R = OMe, D = C(═NH)NH₂ aa₉ R = OMe, D = C(═NH)NH₂ y₁₀ R = F, D = C(O)NH₂ z₁₀ R = F, D = C(O)NH₂ aa₁₀ R = F, D = C(O)NH₂ y₁₁ R = Cl, D = C(O)NH₂ z₁₁ R = Cl, D = C(O)NH₂ aa₁₁ R = Cl, D = C(O)NH₂ y₁₂ R = OMe, D = C(O)NH₂ z₁₂ R = OMe, D = C(O)NH₂ aa₁₂ R = OMe, D = C(O)NH₂

bb₁ R = F, D = NH₂ cc₁ R = F, D = NH₂ dd₁ R = F, D = NH₂ bb₂ R = Cl, D = NH₂ cc₂ R = Cl, D = NH₂ dd₂ R = Cl, D = NH₂ bb₃ R = OMe, D = NH₂ cc₃ R = OMe, D = NH₂ dd₃ R = OMe, D = NH₂ bb₄ R = F, D = CH₂NH₂ cc₄ R = F, D = CH₂NH₂ dd₄ R = F, D = CH₂NH₂ bb₅ R = Cl, D = CH₂NH₂ cc₅ R = Cl, D = CH₂NH₂ dd₅ R = Cl, D = CH₂NH₂ bb₆ R = OMe, D = CH₂NH₂ cc₆ R = OMe, D = CH₂NH₂ dd₆ R = OMe, D = CH₂NH₂ bb₇ R = F, D = C(═NH)NH₂ cc₇ R = F, D = C(═NH)NH₂ dd₇ R = F, D = C(═NH)NH₂ bb₈ R = Cl, D = C(═NH)NH₂ cc₈ R = Cl, D = C(═NH)NH₂ dd₈ R = Cl, D = C(═NH)NH₂ bb₉ R = OMe, D = C(═NH)NH₂ cc₉ R = OMe, D = C(═NH)NH₂ dd₉ R = OMe, D = C(═NH)NH₂ bb₁₀ R = F, D = C(O)NH₂ cc₁₀ R = F, D = C(O)NH₂ dd₁₀ R = F, D = C(O)NH₂ bb₁₁ R = Cl, D = C(O)NH₂ cc₁₁ R = Cl, D = C(O)NH₂ dd₁₁ R = Cl, D = C(O)NH₂ bb₁₂ R = OMe, D = C(O)NH₂ cc₁₂ R = OMe, D = C(O)NH₂ dd₁₂ R = OMe, D = C(O)NH₂

ee₁ R = F, D = CH₂NH₂ ff₁ R = F, D = CH₂NH₂ ff₁ R = F, D = CH₂NH₂ ee₂ R = Cl, D = CH₂NH₂ ff₂ R = Cl, D = CH₂NH₂ gg₂ R = Cl, D = CH₂NH₂ ee₃ R = OMe, D = CH₂NH₂ ff₃ R = OMe, D = CH₂NH₂ gg₃ R = OMe, D = CH₂NH₂ ee₄ R = CH₂NH₂, D = CH₂NH₂ ff₄ R = CH₂NH₂, D = CH₂NH₂ gg₄ R = CH₂NH₂, D = CH₂NH₂

hh₁ R = F, D = CH₂NH₂ ii₁ R = F, D = CH₂NH₂ jj₁ R = F, D = CH₂NH₂ hh₂ R = Cl, D = CH₂NH₂ ii₂ R = Cl, D = CH₂NH₂ jj₂ R = Cl, D = CH₂NH₂ hh₃ R = OMe, D = CH₂NH₂ ii₃ R = OMe, D = CH₂NH₂ jj₃ R = OMe, D = CH₂NH₂ hh₄ R = CH₂NH₂, D = CH₂NH₂ ii₄ R = CH₂NH₂, D = CH₂NH₂ jj₄ R = CH₂NH₂, D = CH₂NH₂

kk₁ R = F, D = CH₂NH₂ ll₁ R = F, D = CH₂NH₂ mm₁ R = F, D = CH₂NH₂ kk₂ R = Cl, D = CH₂NH₂ ll₂ R = Cl, D = CH₂NH₂ mm₂ R = Cl, D = CH₂NH₂ kk₃ R = OMe, D = CH₂NH₂ ll₃ R = OMe, D = CH₂NH₂ mm₃ R = OMe, D = CH₂NH₂ kk₄ R = CH₂NH₂, D = CH₂NH₂ ll₄ R = CH₂NH₂, D = CH₂NH₂ mm₄ R = CH₂NH₂, D = CH₂NH₂

nn₁ R = F, D = CH₂NH₂ oo₁ R = F, D = CH₂NH₂ pp₁ R = F, D = CH₂NH₂ nn₂ R = Cl, D = CH₂NH₂ oo₂ R = Cl, D = CH₂NH₂ pp₂ R = Cl, D = CH₂NH₂ nn₃ R = OMe, D = CH₂NH₂ oo₃ R = OMe, D = CH₂NH₂ pp₃ R = OMe, D = CH₂NH₂ nn₄ R = CH₂NH₂, D = CH₂NH₂ oo₄ R = CH₂NH₂, D = CH₂NH₂ pp₄ R = CH₂NH₂, D = CH₂NH₂

qq₁ R = F, D = CH₂NH₂ rr₁ R = F, D = CH₂NH₂ ss₁ R = F, D = CH₂NH₂ qq₂ R = Cl, D = CH₂NH₂ rr₂ R = Cl, D = CH₂NH₂ ss₂ R = Cl, D = CH₂NH₂ qq₃ R = OMe, D = CH₂NH₂ rr₃ R = OMe, D = CH₂NH₂ ss₃ R = OMe, D = CH₂NH₂ qq₄ R = CH₂NH₂, D = CH₂NH₂ rr₄ R = CH₂NH₂, D = CH₂NH₂ ss₄ R = CH₂NH₂, D = CH₂NH₂ Ex # R^(1b) A B  1 H phenyl 2-((Me)₂N-methyl)phenyl  2 H phenyl 2-((Me)NH-methyl)phenyl  3 H phenyl 2-(H₂N-methyl)phenyl  4 H phenyl 2-HOCH₂-phenyl  5 H 2-F-phenyl 2-((Me)₂N-methyl)phenyl  6 H 2-F-phenyl 2-((Me)NH-methyl)phenyl  7 H 2-F-phenyl 2-(H₂N-methyl)phenyl  8 H 2-F-phenyl 2-HOCH₂-phenyl  9 H phenyl 2-methylimidazol-1-yl  10 H phenyl 2-ethylimidazol-1-yl  11 H phenyl 2-((Me)₂N-methyl)imidazol-1-yl  12 H phenyl 2-CH₃NHSO₂-imidazol-1-yl  13 H phenyl 2-CH₃OCH₂-imidazol-1-yl  14 H 2-F-phenyl 2-methylimidazol-1-yl  15 H 2-F-phenyl 2-ethylimidazol-1-yl  16 H 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  17 H 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl  18 H 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl  19 H 2-Cl-phenyl 2-methylimidazol-1-yl  20 H 2-Cl-phenyl 2-ethylimidazol-1-yl  21 H 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  22 H 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl  23 H 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl  24 H 2-(Me)₂N-phenyl 2-methylimidazol-1-yl  25 H 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl  26 H 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  27 H 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl  28 H 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl  29 H phenyl N-methylimidazol-2-yl  30 H phenyl 4-methylimidazol-5-yl  31 H phenyl 5-CF₃-pyrazol-1-yl  32 H 2-F-phenyl N-methylimidazol-2-yl  33 H 2-F-phenyl 4-methylimidazol-5-yl  34 H 2-F-phenyl 5-CF₃-pyrazol-1-yl  35 H phenyl guanidino  36 H phenyl 2-thiazolin-2-ylamine  37 H phenyl N-methyl-2-imidazolin-2-yl  38 H phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl  39 H phenyl N-methylimidazol-2-ylthiol  40 H phenyl t-butoxycarbonylamine  41 H phenyl (N-pyrrolidino)formylimino  42 H phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino  43 H 2-F-phenyl guanidino  44 H 2-F-phenyl 2-thiazolin-2-ylamine  45 H 2-F-phenyl N-methyl-2-imidazolin-2-yl  46 H 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl  47 H 2-F-phenyl N-methylimidazol-2-ylthio  48 H 2-F-phenyl t-butoxycarbonylamine  49 H 2-F-phenyl (N-pyrrolidino)formylimino  50 H 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino  51 H 2-CH₃O-phenyl (N-pyrrolidino)formylimino  52 H 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino  53 —CN phenyl 2-((Me)₂N-methyl)phenyl  54 —CN phenyl 2-((Me)NH-methyl)phenyl  55 —CN phenyl 2-(H₂N-methyl)phenyl  56 —CN phenyl 2-HOCH₂-phenyl  57 —CN 2-F-phenyl 2-((Me)₂N-methyl)phenyl  58 —CN 2-F-phenyl 2-((Me)NH-methyl)phenyl  59 —CN 2-F-phenyl 2-(H₂N-methyl)phenyl  60 —CN 2-F-phenyl 2-HOCH₂-phenyl  61 —CN phenyl 2-methylimidazol-1-yl  62 —CN phenyl 2-ethylimidazol-1-yl  63 —CN phenyl 2-((Me)₂N-methyl)imidazol-1-yl  64 —CN phenyl 2-CH₃SO₂-imidazol-1-yl  65 —CN phenyl 2-CH₃OCH₂-imidazol-1-yl  66 —CN 2-F-phenyl 2-methylimidazol-1-yl  67 —CN 2-F-phenyl 2-ethylimidazol-1-yl  68 —CN 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  69 —CN 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl  70 —CN 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl  71 —CN 2-Cl-phenyl 2-methylimidazol-1-yl  72 —CN 2-Cl-phenyl 2-ethylimidazol-1-yl  73 —CN 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  74 —CN 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl  75 —CN 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl  76 —CN 2-(Me)₂N-phenyl 2-methylimidazol-1-yl  77 —CN 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl  78 —CN 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl  79 —CN 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl  80 —CN 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl  81 —CN phenyl N-methylimidazol-2-yl  82 —CN phenyl 4-methylimidazol-5-yl  83 —CN phenyl 5-CF₃-pyrazol-1-yl  84 —CN 2-F-phenyl N-methylimidazol-2-yl  85 —CN 2-F-phenyl 4-methylimidazol-5-yl  86 —CN 2-F-phenyl 5-CF₃-pyrazol-1-yl  87 —CN phenyl guanidino  88 —CN phenyl 2-thiazolin-2-ylamine  89 —CN phenyl N-methyl-2-imidazolin-2-yl  90 —CN phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl  91 —CN phenyl N-methylimidazol-2-ylthiol  92 —CN phenyl t-butoxycarbonylamine  93 —CN phenyl (N-pyrrolidino)formylimino  94 —CN phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino  95 —CN 2-F-phenyl guanidino  96 —CN 2-F-phenyl 2-thiazolin-2-ylamine  97 —CN 2-F-phenyl N-methyl-2-imidazolin-2-yl  98 —CN 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl  99 —CN 2-F-phenyl N-methylimidazol-2-ylthio 100 —CN 2-F-phenyl t-butoxycarbonylamine 101 —CN 2-F-phenyl (N-pyrrolidino)formylimino 102 —CN 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 103 —CN 2-CH₃O-phenyl (N-pyrrolidino)formylimino 104 —CN 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 105 CF₃ phenyl 2-((Me)₂N-methyl)phenyl 106 CF₃ phenyl 2-((Me)NH-methyl)phenyl 107 CF₃ phenyl 2-(H₂N-methyl)phenyl 108 CF₃ phenyl 2-HOCH₂-phenyl 109 CF₃ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 110 CF₃ 2-F-phenyl 2-((Me)NH-methyl)phenyl 111 CF₃ 2-F-phenyl 2-(H₂N-methyl)phenyl 112 CF₃ 2-F-phenyl 2-HOCH₂-phenyl 113 CF₃ phenyl 2-methylimidazol-1-yl 114 CF₃ phenyl 2-ethylimidazol-1-yl 115 CF₃ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 116 CF₃ phenyl 2-CH₃SO₂-imidazol-1-yl 117 CF₃ phenyl 2-CH₃OCH₂-imidazol-1-yl 118 CF₃ 2-F-phenyl 2-methylimidazol-1-yl 119 CF₃ 2-F-phenyl 2-ethylimidazol-1-yl 120 CF₃ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 121 CF₃ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 122 CF₃ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 123 CF₃ 2-Cl-phenyl 2-methylimidazol-1-yl 124 CF₃ 2-Cl-phenyl 2-ethylimidazol-1-yl 125 CF₃ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 126 CF₃ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 127 CF₃ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 128 CF₃ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 129 CF₃ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 130 CF₃ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 131 CF₃ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 132 CF₃ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 133 CF₃ phenyl N-methylimidazol-2-yl 134 CF₃ phenyl 4-methylimidazol-5-yl 135 CF₃ phenyl 5-CF₃-pyrazol-1-yl 136 CF₃ 2-F-phenyl N-methylimidazol-2-yl 137 CF₃ 2-F-phenyl 4-methylimidazol-5-yl 138 CF₃ 2-F-phenyl 5-CF₃-pyrazol-1-yl 139 CF₃ phenyl guanidino 140 CF₃ phenyl 2-thiazolin-2-ylamine 141 CF₃ phenyl N-methyl-2-imidazolin-2-yl 142 CF₃ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 143 CF₃ phenyl N-methylimidazol-2-ylthiol 144 CF₃ phenyl t-butoxycarbonylamine 145 CF₃ phenyl (N-pyrrolidino)formylimino 146 CF₃ phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 147 CF₃ 2-F-phenyl guanidino 148 CF₃ 2-F-phenyl 2-thiazolin-2-ylamine 149 CF₃ 2-F-phenyl N-methyl-2-imidazolin-2-yl 150 CF₃ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 151 CF₃ 2-F-phenyl N-methylimidazol-2-ylthio 152 CF₃ 2-F-phenyl t-butoxycarbonylamine 153 CF₃ 2-F-phenyl (N-pyrrolidino)formylimino 154 CF₃ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 155 CF₃ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 156 CF₃ 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 157 CONH₂ phenyl 2-((Me)₂N-methyl)phenyl 158 CONH₂ phenyl 2-((Me)NH-methyl)phenyl 159 CONH₂ phenyl 2-(H₂N-methyl)phenyl 160 CONH₂ phenyl 2-HOCH₂-phenyl 161 CONH₂ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 162 CONH₂ 2-F-phenyl 2-((Me)NH-methyl)phenyl 163 CONH₂ 2-F-phenyl 2-(H₂N-methyl)phenyl 164 CONH₂ 2-F-phenyl 2-HOCH₂-phenyl 165 CONH₂ phenyl 2-methylimidazol-1-yl 166 CONH₂ phenyl 2-ethylimidazol-1-yl 167 CONH₂ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 168 CONH₂ phenyl 2-CH₃SO₂-imidazol-1-yl 169 CONH₂ phenyl 2-CH₃OCH₂-imidazol-1-yl 170 CONH₂ 2-F-phenyl 2-methylimidazol-1-yl 171 CONH₂ 2-F-phenyl 2-ethylimidazol-1-yl 172 CONH₂ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 173 CONH₂ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 174 CONH₂ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 175 CONH₂ 2-Cl-phenyl 2-methylimidazol-1-yl 176 CONH₂ 2-Cl-phenyl 2-ethylimidazol-1-yl 177 CONH₂ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 178 CONH₂ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 179 CONH₂ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 180 CONH₂ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 181 CONH₂ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 182 CONH₂ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 183 CONH₂ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 184 CONH₂ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 185 CONH₂ phenyl N-methylimidazol-2-yl 186 CONH₂ phenyl 4-methylimidazol-5-yl 187 CONH₂ phenyl 5-CF₃-pyrazol-1-yl 188 CONH₂ 2-F-phenyl N-methylimidazol-2-yl 189 CONH₂ 2-F-phenyl 4-methylimidazol-5-yl 190 CONH₂ 2-F-phenyl 5-CF₃-pyrazol-1-yl 191 CONH₂ phenyl guanidino 192 CONH₂ phenyl 2-thiazolin-2-ylamine 193 CONH₂ phenyl N-methyl-2-imidazolin-2-yl 194 CONH₂ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 195 CONH₂ phenyl N-methylimidazol-2-ylthiol 196 CONH₂ phenyl t-butoxycarbonylamine 197 CONH₂ phenyl (N-pyrrolidino)formylimino 198 CONH₂ phenyl (N-pyrrplidino)formyl-N-(methanesulfamoyl)imino 199 CONH₂ 2-F-phenyl guanidino 200 CONH₂ 2-F-phenyl 2-thiazolin-2-ylamine 201 CONH₂ 2-F-phenyl N-methyl-2-imidazolin-2-yl 202 CONH₂ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 203 CONH₂ 2-F-phenyl N-methylimidazol-2-ylthio 204 CONH₂ 2-F-phenyl t-butoxycarbonylamine 205 CONH₂ 2-F-phenyl (N-pyrrolidino)formylimino 206 CONH₂ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 207 CONH₂ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 208 CONH₂ 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 209 SCH₃ phenyl 2-((Me)₂N-methyl)phenyl 210 SCH₃ phenyl 2-((Me)NH-methyl)phenyl 211 SCH₃ phenyl 2-(H₂N-methyl)phenyl 212 SCH₃ phenyl 2-HOCH₂-phenyl 213 SCH₃ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 214 SCH₃ 2-F-phenyl 2-((Me)NH-methyl)phenyl 215 SCH₃ 2-F-phenyl 2-(H₂N-methyl)phenyl 216 SCH₃ 2-F-phenyl 2-HOCH₂-phenyl 217 SCH₃ phenyl 2-methylimidazol-1-yl 218 SCH₃ phenyl 2-ethylimidazol-1-yl 219 SCH₃ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 220 SCH₃ phenyl 2-CH₃SO₂-imidazol-1-yl 221 SCH₃ phenyl 2-CH₃OCH₂-imidazol-1-yl 222 SCH₃ 2-F-phenyl 2-methylimidazol-1-yl 223 SCH₃ 2-F-phenyl 2-ethylimidazol-1-yl 224 SCH₃ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 225 SCH₃ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 226 SCH₃ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 227 SCH₃ 2-Cl-phenyl 2-methylimidazol-1-yl 228 SCH₃ 2-Cl-phenyl 2-ethylimidazol-1-yl 229 SCH₃ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 230 SCH₃ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 231 SCH₃ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 232 SCH₃ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 233 SCH₃ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 234 SCH₃ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 235 SCH₃ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 236 SCH₃ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 237 SCH₃ phenyl N-methylimidazol-2-yl 238 SCH₃ phenyl 4-methylimidazol-5-yl 239 SCH₃ phenyl 5-CF₃-pyrazol-1-yl 240 SCH₃ 2-F-phenyl N-methylimidazol-2-yl 241 SCH₃ 2-F-phenyl 4-methylimidazol-5-yl 242 SCH₃ 2-F-phenyl 5-CF₃-pyrazol-1-yl 243 SCH₃ phenyl guanidino 244 SCH₃ phenyl 2-thiazolin-2-ylamine 245 SCH₃ phenyl N-methyl-2-imidazolin-2-yl 246 SCH₃ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 247 SCH₃ phenyl N-methylimidazol-2-ylthiol 248 SCH₃ phenyl t-butoxycarbonylamine 249 SCH₃ phenyl (N-pyrrolidino)formylimino 250 SCH₃ phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 251 SCH₃ 2-F-phenyl guanidino 252 SCH₃ 2-F-phenyl 2-thiazolin-2-ylamine 253 SCH₃ 2-F-phenyl N-methyl-2-imidazolin-2-yl 254 SCH₃ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 255 SCH₃ 2-F-phenyl N-methylimidazol-2-ylthio 256 SCH₃ 2-F-phenyl t-butoxycarbonylamine 257 SCH₃ 2-F-phenyl (N-pyrrolidino)formylimino 258 SCH₃ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 259 SCH₃ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 260 SCH₃ 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 261 SO₂CH₃ phenyl 2-((Me)₂N-methyl)phenyl 262 SO₂CH₃ phenyl 2-((Me)NH-methyl)phenyl 263 SO₂CH₃ phenyl 2-(H₂N-methyl)phenyl 264 SO₂CH₃ phenyl 2-HOCH₂-phenyl 265 SO₂CH₃ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 266 SO₂CH₃ 2-F-phenyl 2-((Me)NH-methyl)phenyl 267 SO₂CH₃ 2-F-phenyl 2-(H₂N-methyl)phenyl 268 SO₂CH₃ 2-F-phenyl 2-HOCH₂-phenyl 269 SO₂CH₃ phenyl 2-methylimidazol-1-yl 270 SO₂CH₃ phenyl 2-ethylimidazol-1-yl 271 SO₂CH₃ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 272 SO₂CH₃ phenyl 2-CH₃SO₂-imidazol-1-yl 273 SO₂CH₃ phenyl 2-CH₃OCH₂-imidazol-1-yl 274 SO₂CH₃ 2-F-phenyl 2-methylimidazol-1-yl 275 SO₂CH₃ 2-F-phenyl 2-ethylimidazol-1-yl 276 SO₂CH₃ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-1yl 277 SO₂CH₃ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 278 SO₂CH₃ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 279 SO₂CH₃ 2-Cl-phenyl 2-methylimidazol-1-yl 280 SO₂CH₃ 2-Cl-phenyl 2-ethylimidazol-1-yl 281 SO₂CH₃ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 282 SO₂CH₃ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 283 SO₂CH₃ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 284 SO₂CH₃ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 285 SO₂CH₃ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 286 SO₂CH₃ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 287 SO₂CH₃ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 288 SO₂CH₃ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 289 SO₂CH₃ phenyl N-methylimidazol-2-yl 290 SO₂CH₃ phenyl 4-methylimidazol-5-yl 291 SO₂CH₃ phenyl 5-CF₃-pyrazol-1-yl 292 SO₂CH₃ 2-F-phenyl N-methylimidazol-2-yl 293 SO₂CH₃ 2-F-phenyl 4-methylimidazol-5-yl 294 SO₂CH₃ 2-F-phenyl 5-CF₃-pyrazol-1-yl 295 SO₂CH₃ phenyl guanidino 296 SO₂CH₃ phenyl 2-thiazolin-2-ylamine 297 SO₂CH₃ phenyl N-methyl-2-imidazolin-2-yl 298 SO₂CH₃ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 299 SO₂CH₃ phenyl N-methylimidazol-2-ylthiol 300 SO₂CH₃ phenyl t-butoxycarbonylamine 301 SO₂CH₃ phenyl (N-pyrrolidino)formylimino 302 SO₂CH₃ phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 303 SO₂CH₃ 2-F-phenyl guanidino 304 SO₂CH₃ 2-F-phenyl 2-thiazolin-2-ylamine 305 SO₂CH₃ 2-F-phenyl N-methyl-2-imidazolin-2-yl 306 SO₂CH₃ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 307 SO₂CH₃ 2-F-phenyl N-methylimidazol-2-ylthio 308 SO₂CH₃ 2-F-phenyl t-butoxycarbonylamine 309 SO₂CH₃ 2-F-phenyl (N-pyrrolidino)formylimino 310 SO₂CH₃ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 311 SO₂CH₃ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 312 SO₂CH₃ 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 313 NHSO₂CH₃ phenyl 2-((Me)₂N-methyl)phenyl 314 NHSO₂CH₃ phenyl 2-((Me)NH-methyl)phenyl 315 NHSO₂CH₃ phenyl 2-(H₂N-methyl)phenyl 316 NHSO₂CH₃ phenyl 2-HOCH₂-phenyl 317 NHSO₂CH₃ 2-F-phenyl 2-((Me)₂N-methyl)phenyl 318 NHSO₂CH₃ 2-F-phenyl 2-((Me)NH-methyl)phenyl 319 NHSO₂CH₃ 2-F-phenyl 2-(H₂N-methyl)phenyl 320 NHSO₂CH₃ 2-F-phenyl 2-HOCH₂-phenyl 321 NHSO₂CH₃ phenyl 2-methylimidazol-1-yl 322 NHSO₂CH₃ phenyl 2-ethylimidazol-1-yl 323 NHSO₂CH₃ phenyl 2-((Me)₂N-methyl)imidazol-1-yl 324 NHSO₂CH₃ phenyl 2-CH₃SO₂-imidazol-1-yl 325 NHSO₂CH₃ phenyl 2-CH₃OCH₂-imidazol-1-yl 326 NHSO₂CH₃ 2-F-phenyl 2-methylimidazol-1-yl 327 NHSO₂CH₃ 2-F-phenyl 2-ethylimidazol-1-yl 328 NHSO₂CH₃ 2-F-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 329 NHSO₂CH₃ 2-F-phenyl 2-CH₃SO₂-imidazol-1-yl 330 NHSO₂CH₃ 2-F-phenyl 2-CH₃OCH₂-imidazol-1-yl 331 NHSO₂CH₃ 2-Cl-phenyl 2-methylimidazol-1-yl 332 NHSO₂CH₃ 2-Cl-phenyl 2-ethylimidazol-1-yl 333 NHSO₂CH₃ 2-Cl-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 334 NHSO₂CH₃ 2-Cl-phenyl 2-CH₃SO₂-imidazol-1-yl 335 NHSO₂CH₃ 2-Cl-phenyl 2-CH₃OCH₂-imidazol-1-yl 336 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-methylimidazol-1-yl 337 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-ethylimidazol-1-yl 338 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-((Me)₂N-methyl)imidazol-1-yl 339 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-CH₃SO₂-imidazol-1-yl 340 NHSO₂CH₃ 2-(Me)₂N-phenyl 2-CH₃OCH₂-imidazol-1-yl 341 NHSO₂CH₃ phenyl N-methylimidazol-2-yl 342 NHSO₂CH₃ phenyl 4-methylimidazol-5-yl 343 NHSO₂CH₃ phenyl 5-CF₃-pyrazol-1-yl 344 NHSO₂CH₃ 2-F-phenyl N-methylimidazol-2-yl 345 NHSO₂CH₃ 2-F-phenyl 4-methylimidazol-5-yl 346 NHSO₂CH₃ 2-F-phenyl 5-CF₃-pyrazol-1-yl 347 NHSO₂CH₃ phenyl guanidino 348 NHSO₂CH₃ phenyl 2-thiazolin-2-ylamine 349 NHSO₂CH₃ phenyl N-methyl-2-imidazolin-2-yl 350 NHSO₂CH₃ phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 351 NHSO₂CH₃ phenyl N-methylimidazol-2-ylthiol 352 NHSO₂CH₃ phenyl t-butoxycarbonylamine 353 NHSO₂CH₃ phenyl (N-pyrrolidino)formylimino 354 NHSO₂CH₃ phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 355 NHSO₂CH₃ 2-F-phenyl guanidino 356 NHSO₂CH₃ 2-F-phenyl 2-thiazolin-2-ylamine 357 NHSO₂CH₃ 2-F-phenyl N-methyl-2-imidazolin-2-yl 358 NHSO₂CH₃ 2-F-phenyl N-methyl-1,4,5,6-tetrahydropyrimid-2-yl 359 NHSO₂CH₃ 2-F-phenyl N-methylimidazol-2-ylthio 360 NHSO₂CH₃ 2-F-phenyl t-butoxycarbonylamine 361 NHSO₂CH₃ 2-F-phenyl (N-pyrrolidino)formylimino 362 NHSO₂CH₃ 2-F-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino 363 NHSO₂CH₃ 2-CH₃O-phenyl (N-pyrrolidino)formylimino 364 NHSO₂CH₃ 2-CH₃O-phenyl (N-pyrrolidino)formyl-N-(methanesulfamoyl)imino

Utility

The compounds of this invention are useful as anticoagulants for the treatment or prevention of thromboembolic disorders in mammals. The term “thromboembolic disorders” as used herein includes arterial or venous cardiovascular or cerebrovascular thromboembolic disorders, including, for example, unstable angina, first or recurrent myocardial infarction, ischemic sudden death, transient ischemic attack, stroke, atherosclerosis, venous thrombosis, deep vein thrombosis, thrombophlebitis, arterial embolism, coronary and cerebral arterial thrombosis, cerebral embolism, kidney embolisms, and pulmonary embolisms. The anticoagulant effect of compounds of the present invention is believed to be due to inhibition of factor Xa or thrombin.

The effectiveness of compounds of the present invention as inhibitors of factor Xa was determined using purified human factor Xa and synthetic substrate. The rate of factor Xa hydrolysis of chromogenic substrate S2222 (Kabi Pharmacia, Franklin, Ohio) was measured both in the absence and presence of compounds of the present invention. Hydrolysis of the substrate resulted in the release of pNA, which was monitored spectrophotometrically by measuring the increase in absorbance at 405 nM. A decrease in the rate of absorbance change at 405 nm in the presence of inhibitor is indicative of enzyme inhibition. The results of this assay are expressed as inhibitory constant, K_(i).

Factor Xa determinations were made in 0.10 M sodium phosphate buffer, pH 7.5, containing 0.20 M NaCl, and 0.5% PEG 8000. The Michaelis constant, K_(m), for substrate hydrolysis was determined at 25° C. using the method of Lineweaver and Burk. Values of K_(i) were determined by allowing 0.2-0.5 nM human factor Xa (Enzyme Research Laboratories, South Bend, Ind.) to react with the substrate (0.20 mM-1 mM) in the presence of inhibitor. Reactions were allowed to go for 30 minutes and the velocities (rate of absorbance change vs time) were measured in the time frame of 25-30 minutes. The following relationship was used to calculate K_(i) values:

(v _(o) −v _(s))/v _(s) =I/(K _(i)(1+S/K _(m)))

where:

v_(o) is the velocity of the control in the absence of inhibitor;

v_(s) is the velocity in the presence of inhibitor;

I is the concentration of inhibitor;

K_(i) is the dissociation constant of the enzyme:inhibitor complex;

S is the concentration of substrate;

K_(m) is the Michaelis constant.

Using the methodology described above, a number of compounds of the present invention were found to exhibit a K_(i) of ≦15 μM, thereby confirming the utility of the compounds of the present invention as effective Xa inhibitors.

The antithrombotic effect of compounds of the present invention can be demonstrated in a rabbit arterio-venous (AV) shunt thrombosis model. In this model, rabbits weighing 2-3 kg anesthetized with a mixture of xylazine (10 mg/kg i.m.) and ketamine (50 mg/kg i.m.) are used. A saline-filled AV shunt device is connected between the femoral arterial and the femoral venous cannulae. The AV shunt device consists of a piece of 6-cm tygon tubing which contains a piece of silk thread. Blood will flow from the femoral artery via the AV-shunt into the femoral vein. The exposure of flowing blood to a silk thread will induce the formation of a significant thrombus. After forty minutes, the shunt is disconnected and the silk thread covered with thrombus is weighed. Test agents or vehicle will be given (i.v., i.p., s.c., or orally) prior to the opening of the AV shunt. The percentage inhibition of thrombus formation is determined for each treatment group. The ID50 values (dose which produces 50% inhibition of thrombus formation) are estimated by linear regression.

The compounds of formula (I) may also be useful as inhibitors of serine proteases, notably human thrombin, plasma kallikrein and plasmin. Because of their inhibitory action, these compounds are indicated for use in the prevention or treatment of physiological reactions, blood coagulation and inflammation, catalyzed by the aforesaid class of enzymes. Specifically, the compounds have utility as drugs for the treatment of diseases arising from elevated thrombin activity such as myocardial infarction, and as reagents used as anticoagulants in the processing of blood to plasma for diagnostic and other commercial purposes.

Some compounds of the present invention were shown to be direct acting inhibitors of the serine protease thrombin by their ability to inhibit the cleavage of small molecule substrates by thrombin in a purified system. In vitro inhibition constants were determined by the method described by Kettner et al. in J. Biol. Chem. 265, 18289-18297 (1990), herein incorporated by reference. In these assays, thrombin-mediated hydrolysis of the chromogenic substrate S2238 (Helena Laboratories, Beaumont, Tex.) was monitored spectrophotometrically. Addition of an inhibitor to the assay mixture results in decreased absorbance and is indicative of thrombin inhibition. Human thrombin (Enzyme Research Laboratories, Inc., South Bend, Ind.) at a concentration of 0.2 nM in 0.10 M sodium phosphate buffer, pH 7.5, 0.20 M NaCl, and 0.5% PEG 6000, was incubated with various substrate concentrations ranging from 0.20 to 0.02 mM. After 25 to 30 minutes of incubation, thrombin activity was assayed by monitoring the rate of increase in absorbance at 405 nm which arises owing to substrate hydrolysis. Inhibition constants were derived from reciprocal plots of the reaction velocity as a function of substrate concentration using the standard method of Lineweaver and Burk. Using the methodology described above, some compounds of this invention were evaluated and found to exhibit a K_(i) of less than 15 μm, thereby confirming the utility of the compounds of the present invention as effective Xa inhibitors.

The compounds of the present invention can be administered alone or in combination with one or more additional therapeutic agents. These include other anti-coagulant or coagulation inhibitory agents, anti-platelet or platelet inhibitory agents, thrombin inhibitors, or thrombolytic or fibrinolytic agents.

The compounds are administered to a mammal in a therapeutically effective amount. By “therapeutically effective amount” it is meant an amount of a compound of Formula I that, when administered alone or in combination with an additional therapeutic agent to a mammal, is effective to prevent or ameliorate the thromboembolic disease condition or the progression of the disease.

By “administered in combination” or “combination therapy” it is meant that the compound of Formula I and one or more additional therapeutic agents are administered concurrently to the mammal being treated. When administered in combination each component may be administered at the same time or sequentially in any order at different points in time. Thus, each component may be administered separately but sufficiently closely in time so as to provide the desired therapeutic effect. Other anticoagulant agents (or coagulation inhibitory agents) that may be used in combination with the compounds of this invention include warfarin and heparin, as well as other factor Xa inhibitors such as those described in the publications identified above under Background of the Invention.

The term anti-platelet agents (or platelet inhibitory agents), as used herein, denotes agents that inhibit platelet function such as by inhibiting the aggregation, adhesion or granular secretion of platelets. Such agents include, but are not limited to, the various known non-steroidal anti-inflammatory drugs (NSAIDS) such as aspirin, ibuprofen, naproxen, sulindac, indomethacin, mefenamate, droxicam, diclofenac, sulfinpyrazone, and piroxicam, including pharmaceutically acceptable salts or prodrugs thereof. Of the NSAIDS, aspirin (acetylsalicyclic acid or ASA), and piroxicam are preferred. Other suitable anti-platelet agents include ticlopidine, including pharmaceutically acceptable salts or prodrugs thereof. Ticlopidine is also a preferred compound since it is known to be gentle on the gastro-intestinal tract in use. Still other suitable platelet inhibitory agents include IIb/IIIa antagonists, thromboxane-A2-receptor antagonists and thromboxane-A2-synthetase inhibitors, as well as pharmaceutically acceptable salts or prodrugs thereof.

The term thrombin inhibitors (or anti-thrombin agents), as used herein, denotes inhibitors of the serine protease thrombin. By inhibiting thrombin, various thrombin-mediated processes, such as thrombin-mediated platelet activation (that is, for example, the aggregation of platelets, and/or the granular secretion of plasminogen activator inhibitor-1 and/or serotonin) and/or fibrin formation are disrupted. A number of thrombin inhibitors are known to one of skill in the art and these inhibitors are contemplated to be used in combination with the present compounds. Such inhibitors include, but are not limited to, boroarginine derivatives, boropeptides, heparins, hirudin and argatroban, including pharmaceutically acceptable salts and prodrugs thereof. Boroarginine derivatives and boropeptides include N-acetyl and peptide derivatives of boronic acid, such as C-terminal a-aminoboronic acid derivatives of lysine, ornithine, arginine, homoarginine and corresponding isothiouronium analogs thereof. The term hirudin, as used herein, includes suitable derivatives or analogs of hirudin, referred to herein as hirulogs, such as disulfatohirudin. Boropeptide thrombin inhibitors include compounds described in Kettner et al., U.S. Pat. No. 5,187,157 and European Patent Application Publication Number 293 881 A2, the disclosures of which are hereby incorporated herein by reference. Other suitable boroarginine derivatives and boropeptide thrombin inhibitors include those disclosed in PCT Application Publication Number 92/07869 and European Patent Application Publication Number 471,651 A2, the disclosures of which are hereby incorporated herein by reference.

The term thrombolytics (or fibrinolytic) agents (or thrombolytics or fibrinolytics), as used herein, denotes agents that lyse blood clots (thrombi). Such agents include tissue plasminogen activator, anistreplase, urokinase or streptokinase, including pharmaceutically acceptable salts or prodrugs thereof. The term anistreplase, as used herein, refers to anisoylated plasminogen streptokinase activator complex, as described, for example, in European Patent Application No. 028,489, the disclosure of which is hereby incorporated herein by reference herein. The term urokinase, as used herein, is intended to denote both dual and single chain urokinase, the latter also being referred to herein as prourokinase.

Administration of the compounds of Formula I of the invention in combination with such additional therapeutic agent, may afford an efficacy advantage over the compounds and agents alone, and may do so while permitting the use of lower doses of each. A lower dosage minimizes the potential of side effects, thereby providing an increased margin of safety.

The compounds of the present invention are also useful as standard or reference compounds, for example as a quality standard or control, in tests or assays involving the inhibition of factor Xa. Such compounds may be provided in a commercial kit, for example, for use in pharmaceutical research involving factor Xa. For example, a compound of the present invention could be used as a reference in an assay to compare its known activity to a compound with an unknown activity. This would ensure the experimenter that the assay was being performed properly and provide a basis for comparison, especially if the test compound was a derivative of the reference compound. When developing new assays or protocols, compounds according to the present invention could be used to test their effectiveness.

The compounds of the present invention may also be used in diagnostic assays involving factor Xa. For example, the presence of factor Xa in an unknown sample could be determined by addition of chromogenic substrate S2222 to a series of solutions containing test sample and optionally one of the compounds of the present invention. If production of pNA is observed in the solutions containing test sample, but no compound of the present invention, then one would conclude factor Xa was present.

Dosage and Formulation

The compounds of this invention can be administered in such oral dosage forms as tablets, capsules (each of which includes sustained release or timed release formulations), pills, powders, granules, elixirs, tinctures, suspensions, syrups, and emulsions. They may also be administered in intravenous (bolus or infusion), intraperitoneal, subcutaneous, or intramuscular form, all using dosage forms well known to those of ordinary skill in the pharmaceutical arts. They can be administered alone, but generally will be administered with a pharmaceutical carrier selected on the basis of the chosen route of administration and standard pharmaceutical practice.

The dosage regimen for the compounds of the present invention will, of course, vary depending upon known factors, such as the pharmacodynamic characteristics of the particular agent and its mode and route of administration; the species, age, sex, health, medical condition, and weight of the recipient; the nature and extent of the symptoms; the kind of concurrent treatment; the frequency of treatment; the route of administration, the renal and hepatic function of the patient, and the effect desired. A physician or veterinarian can determine and prescribe the effective amount of the drug required to prevent, counter, or arrest the progress of the thromboembolic disorder.

By way of general guidance, the daily oral dosage of each active ingredient, when used for the indicated effects, will range between about 0.001 to 1000 mg/kg of body weight, preferably between about 0.01 to 100 mg/kg of body weight per day, and most preferably between about 1.0 to 20 mg/kg/day. Intravenously, the most preferred doses will range from about 1 to about 10 mg/kg/minute during a constant rate infusion. Compounds of this invention may be administered in a single daily dose, or the total daily dosage may be administered in divided doses of two, three, or four times daily.

Compounds of this invention can be administered in intranasal form via topical use of suitable intranasal vehicles, or via transdermal routes, using transdermal skin patches. When administered in the form of a transdermal delivery system, the dosage administration will, of course, be continuous rather than intermittent throughout the dosage regimen.

The compounds are typically administered in admixture with suitable pharmaceutical diluents, excipients, or carriers (collectively referred to herein as pharmaceutical carriers) suitably selected with respect to the intended form of administration, that is, oral tablets, capsules, elixirs, syrups and the like, and consistent with conventional pharmaceutical practices.

For instance, for oral administration in the form of a tablet or capsule, the active drug component can be combined with an oral, non-toxic, pharmaceutically acceptable, inert carrier such as lactose, starch, sucrose, glucose, methyl callulose, magnesium stearate, dicalcium phosphate, calcium sulfate, mannitol, sorbitol and the like; for oral administration in liquid form, the oral drug components can be combined with any orali non-toxic, pharmaceutically acceptable inert carrier such as ethanol, glycerol, water, and the like. Moreover, when desired or necessary, suitable binders, lubricants, disintegrating agents, and coloring agents can also be incorporated into the mixture. Suitable binders include starch, gelatin, natural sugars such as glucose or beta-lactose, corn sweeteners, natural and synthetic gums such as acacia, tragacanth, or sodium alginate, carboxymethylcellulose, polyethylene glycol, waxes, and the like. Lubricants used in these dosage forms include sodium oleate, sodium stearate, magnesium stearate, sodium benzoate, sodium acetate, sodium chloride, and the like. Disintegrators include, without limitation, starch, methyl cellulose, agar, bentonite, xanthan gum, and the like.

The compounds of the present invention can also be administered in the form of liposome delivery systems, such as small unilamellar vesicles, large unilamellar vesicles, and multilamellar vesicles. Liposomes can be formed from a variety of phospholipids, such as cholesterol, stearylamine, or phosphatidylcholines.

Compounds of the present invention may also be coupled with soluble polymers as targetable drug carriers. Such polymers can include polyvinylpyrrolidone, pyran copolymer, polyhydroxypropylmethacrylamide-phenol, polyhydroxyethylaspartamidephenol, or polyethyleneoxide-polylysine substituted with palmitoyl residues. Furthermore, the compounds of the present invention may be coupled to a class of biodegradable polymers useful in achieving controlled release of a drug, for example, polylactic acid, polyglycolic acid, copolymers of polylactic and polyglycolic acid, polyepsilon caprolactone, polyhydroxy butyric acid, polyorthoesters, polyacetals, polydihydropyrans, polycyanoacylates, and crosslinked or amphipathic block copolymers of hydrogels.

Dosage forms (pharmaceutical compositions) suitable for administration may contain from about 1 milligram to about 100 milligrams of active ingredient per dosage unit. In these pharmaceutical compositions the active ingredient will ordinarily be present in an amount of about 0.5-95% by weight based on the total weight of the composition.

Gelatin capsules may contain the active ingredient and powdered carriers, such as lactose, starch, cellulose derivatives, magnesium stearate, stearic acid, and the like. Similar diluents can be used to make compressed tablets. Both tablets and capsules can be manufactured as sustained release products to provide for continuous release of medication over a period of hours. Compressed tablets can be sugar coated or film coated to mask any unpleasant taste and protect the tablet from the atmosphere, or enteric coated for selective disintegration in the gastrointestinal tract.

Liquid dosage forms for oral administration can contain coloring and flavoring to increase patient acceptance.

In general, water, a suitable oil, saline, aqueous dextrose (glucose), and related sugar solutions and glycols such as propylene glycol or polyethylene glycols are suitable carriers for parenteral solutions. Solutions for parenteral administration preferably contain a water soluble salt of the active ingredient, suitable stabilizing agents, and if necessary, buffer substances. Antioxidizing agents such as sodium bisulfite, sodium sulfite, or ascorbic acid, either alone or combined, are suitable stabilizing agents. Also used are citric acid and its salts and sodium EDTA. In addition, parenteral solutions can contain preservatives, such as benzalkonium chloride, methyl- or propyl-paraben, and chlorobutanol.

Suitable pharmaceutical carriers are described in Remington's Pharmaceutical Sciences, Mack Publishing Company, a standard reference text in this field.

Representative useful pharmaceutical dosage-forms for administration of the compounds of this invention can be illustrated as follows:

Capsules

A large number of unit capsules can be prepared by filling standard two-piece hard gelatin capsules each with 100 milligrams of powdered active ingredient, 150 milligrams of lactose, 50 milligrams of cellulose, and 6 milligrams magnesium stearate.

Soft Gelatin Capsules

A mixture of active ingredient in a digestable oil such as soybean oil, cottonseed oil or olive oil may be prepared and injected by means of a positive displacement pump into gelatin to form soft gelatin capsules containing 100 milligrams of the active ingredient. The capsules should be washed and dried.

Tablets

Tablets may be prepared by conventional procedures so that the dosage unit is 100 milligrams of active ingredient, 0.2 milligrams of colloidal silicon dioxide, 5 milligrams of magnesium stearate, 275 milligrams of microcrystalline cellulose, 11 milligrams of starch and 98.8 milligrams of lactose. Appropriate coatings may be applied to increase palatability or delay absorption.

Injectable

A parenteral composition suitable for administration by injection may be prepared by stirring 1.5% by weight of active ingredient in 10% by volume propylene glycol and water. The solution should be made isotonic with sodium chloride and sterilized.

Suspension

An aqueous suspension can be prepared for oral administration so that each 5 mL contain 100 mg of finely divided active ingredient, 200 mg of sodium carboxymethyl cellulose, 5 mg of sodium benzoate, 1.0 g of sorbitol solution, U.S.P., and 0.025 mL of vanillin.

Where the compounds of this invention are combined with other anticoagulant agents, for example, a daily dosage may be about 0.1 to 100 milligrams of the compound of Formula I and about 1 to 7.5 milligrams of the second anticoagulant, per kilogram of patient body weight. For a tablet dosage form, the compounds of this invention generally may be present in an amount of about 5 to 10 milligrams per dosage unit, and the second anti-coagulant in an amount of about 1 to 5 milligrams per dosage unit.

Where the compounds of Formula I are administered in combination with an anti-platelet agent, by way of general guidance, typically a daily dosage may be about 0.01 to 25 milligrams of the compound of Formula I and about 50 to 150 milligrams of the anti-platelet agent, preferably about 0.1 to 1 milligrams of the compound of Formula I and about 1 to 3 milligrams of antiplatelet agents, per kilogram of patient body weight.

Where the compounds of Formula I are adminstered in combination with thrombolytic agent, typically a daily dosage may be about 0.1 to 1 milligrams of the compound of Formula I, per kilogram of patient body weight and, in the case of the thrombolytic agents, the usual dosage of the thrombolyic agent when administered alone may be reduced by about 70-80% when administered with a compound of Formula I.

Where two or more of the foregoing second therapeutic agents are administered with the compound of Formula I, generally the amount of each component in a typical daily dosage and typical dosage form may be reduced relative to the usual dosage of the agent when administered alone, in view of the additive or synergistic effect of the therapeutic agents when administered in combination.

Particularly when provided as a single dosage unit, the potential exists for a chemical interaction between the combined active ingredients. For this reason, when the compound of Formula I and a second therapeutic agent are combined in a single dosage unit they are formulated such that although the active ingredients are combined in a single dosage unit, the physical contact between the active ingredients is minimized (that is, reduced). For example, one active ingredient may be enteric coated. By enteric coating one of the active ingredients, it is possible not only to minimize the contact between the combined active ingredients, but also, it is possible to control the release of one of these components in the gastrointestinal tract such that one of these components is not released in the stomach but rather is released in the intestines. One of the active ingredients may also be coated with a material which effects a sustained-release throughout the gastrointestinal tract and also serves to minimize physical contact between the combined active ingredients. Furthermore, the sustained-released component can be additionally enteric coated such that the release of this component occurs only in the intestine. Still another approach would involve the formulation of a combination product in which the one component is coated with a sustained and/or enteric release polymer, and the other component is also coated with a polymer such as a low viscosity grade of hydroxypropyl methylcellulose (HPMC) or other appropriate materials as known in the art, in order to further separate the active components. The polymer coating serves to form an additional barrier to interaction with the other component.

These as well as other ways of minimizing contact between the components of combination products of the present invention, whether administered in a single dosage form or administered in separate forms but at the same time by the same manner, will be readily apparent to those skilled in the art, once armed with the present disclosure.

Obviously, numerous modifications and variations of the present invention are possible in light of the above teachings. It is therefore to be understood that within the scope of the appended claims, the invention may be practiced otherwise that as specifically described herein. 

What is claimed as new and desired to be secured by Letter Patent of United States is:
 1. A compound of formula I:

or a stereoisomer or pharmaceutically acceptable salt form thereof, wherein; ring M is of formula h or i:

D is selected from CN, C(═NR⁷)NR⁸R⁹, NHC(═NR⁷)NR⁸R⁹, NR⁸CH(═NR⁷), C(O)NR⁸R⁹, and (CR⁸R⁹)NR⁸R⁹; E is selected from phenyl, 2-pyridyl, 4-pyridyl, pyrimidyl, and piperidinyl substituted with 1 R; R is selected from H, F, Cl, Br, I, OR³, SR³, CO₂R³, NO₂, and CH₂OR³, and (CR⁸R⁹)_(t)NR⁸R⁹; alternatively, E and R combine to form methylenedioxy or ethylenedioxy; Z is selected from a bond, C₁₋₄ alkylene, (CH₂)_(r)O(CH₂)_(r), (CH₂)_(r)NR³(CH₂)_(r), (CH₂)_(r)C(O) (CH₂)_(r), (CH₂)_(r)C(O)O(CH₂)_(r), (CH₂)_(r)OC(O) (CH₂)_(r), (CH₂)_(r)C(O)NR³(CH₂)_(r), (CH₂)_(r)NR³C(O) (CH₂)_(r), (CH₂)_(r)OC(O)O(CH₂)_(r), (CH₂)_(r)OC (O)NR³ (CH₂)_(r), (CH₂)_(r)NR³C(O)O (CH₂)_(r), (CH₂)_(r)NR³C(O)NR³(CH₂)_(r), (CH₂)_(r)S(O)_(p)(CH₂)_(r), (CH₂)_(r)SO₂NR³(CH₂)_(r), (CH₂)_(r)NR³SO₂(CH₂)_(r), and (CH₂)_(r)NR³SO₂NR³ (CH₂)_(r), provided that Z does not form a N—N, N—O, N—S, NCH₂N, NCH₂O, or NCH₂S bond with ring M or group A; R^(1a) and R^(1b) are independently absent or selected from —(CH₂)_(r)—R^(1′), —CH═CH—R^(1′), NCH₂R^(1″), OCH₂R^(1″), SCH₂R^(1″), NH(CH₂)₂(CH₂)_(t)R^(1′), O(CH₂)₂(CH₂)_(t)R^(1′), and S(CH₂)₂(CH₂)_(t)R^(1′); alternatively, R^(1a) and R^(1b), when attached to adjacent carbon atoms, together with the atoms to which they are attached form a 5-8 membered saturated, partially saturated or unsaturated ring substituted with 0-2 R⁴ and which contains from 0-2 heteroatoms selected from the group consisting of N, O, and S; alternatively, when Z is C(O)NH and R^(1a) is attached to a ring carbon adjacent to Z, then R^(1a) is a C(O) which replaces the amide hydrogen of Z to form a cyclic imide; R^(1′) is selected from H, C₁₋₃ alkyl, F, Cl, Br, I, —CN, —CHO, (CF₂)_(r)CF₃, (CH₂)_(r)OR², NR²R^(2a), C(O)R^(2c), OC(O)R², (CF₂)_(r)CO₂R^(2c), S(O)_(p)R^(2b), NR²(CH₂)_(r)OR², CH(═NR^(2c))NR²R ^(2a), NR²C(O)R^(2b), NR²C(O)NHR^(2b), NR²C(O)₂R^(2a), OC(O)NR^(2a)R^(2b), C(O)NR²R^(2a), C(O)NR²(CH₂)_(r)OR², SO₂NR²R^(2a), NR²SO₂R^(2b), C₃₋₆ carbocyclic residue substituted with 0-2 R⁴, and 5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R⁴; R^(1″) is selected from H, CH(CH₂OR²)₂, C(O)R^(2c), C(O)NR²R^(2a), S(O)R^(2b), S(O)₂R^(2b), and SO₂NR²R^(2a); R², at each occurrence, is selected from H, CF₃, C₁₋₆ alkyl, benzyl, C₃₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b); R^(2a), at each occurrence, is selected from H, CF₃, C₁₋₆ alkyl, benzyl, phenethyl, C₃₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b); R^(2b), at each occurrence, is selected from CF₃, C₁₋₄ alkoxy, C₁₋₆ alkyl, benzyl, C₃₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b); R^(2c), at each occurrence, is selected from CF₃, OH, C₁₋₄ alkoxy, C₁₋₆ alkyl, benzyl, C₃₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b); alternatively, R² and R^(2a), together with the atom to which they are attached, combine to form a 5 or 6 membered saturated, partially saturated or unsaturated ring substituted with 0-2 R^(4b) and containing from 0-1 additional heteroatoms selected from the group consisting of N, O, and S; R³, at each occurrence, is selected from H, C₁₋₄ alkyl, and phenyl; R^(3a), at each occurrence, is selected from H, C₁₋₄ alkyl, and phenyl; R^(3b), at each occurrence, is selected from H, C₁₋₄ alkyl, and phenyl; R^(3c), at each occurrence, is selected from C₁₋₄ alkyl, and phenyl; A is selected from: C₃₋₁₀ carbocyclic residue substituted with 0-2 R⁴, and 5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R⁴; B is selected from: Y and X-Y; X is selected from C₁₋₄ alkylene, —CR²(CR²R^(2b)) (CH₂)_(t)—, —C(O)—, —C(═NR_(1″))—, —CR²(NR^(1″)R²)—, —CR² (OR²)—, —CR²(SR²)—, —C(O) CR²R^(2a)—, —CR²R^(2a)C(O), —S(O)_(p)—, —S(O)_(p)CR²R^(2a)—, —CR²R^(2a)S(O)_(p)—, —S(O)₂NR²—, —NR²S(O)₂—, —NR²S(O)₂CR²R^(2a)—, —CR²R^(2a)S(O)₂NR²—, —NR²S(O)₂NR²—, —C(O)NR²—, —NR²C(O)—, —C(O)NR²CR²R^(2a)—, —NR²C(O)CR²R^(2a)—, —CR²R^(2a)C(O)NR²—, —CR²R^(2a)NR²C(O)—, —NR²C(O)O—, —OC(O)NR²—, —NR²C(O)NR²—, —NR²—, —NR²CR²R^(2a)—, —CR²R^(2a)NR²—, O, —CR²R^(2a)O—, and —OCR²R^(2a)—; Y is selected from: C₃₋₁₀ carbocyclic residue substituted with 0-2 R^(4a) and 5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4a); R⁴, at each occurrence, is selected from H, ═O, (CH₂)_(r)OR², F, Cl, Br, I, C₁₋₄ alkyl, —CN, NO₂, (CH₂)_(r)NR²R^(2a), (CH₂)_(r)C(O)R^(2c), NR²C(O)R^(2b), C(O)NR²R^(2a), NR²C(O)NR²R^(2a), CH(═NR²)NR²R^(2a), CH(═NS(O)₂R⁵)NR²R^(2a), NHC(═NR²)NR²R^(2a), C(O)NHC(═NR²)NR²R^(2a), SO₂NR²R^(2a), NR²SO₂NR²R^(2a), NR²SO₂—C₁₋₄ alkyl, NR²SO₂R⁵, S(O)_(p)R⁵, (CF₂)_(r)CF₃, NCH₂R^(1″), OCH₂R^(1″), SCH₂R^(1″), N(CH₂)₂(CH₂)_(t)R^(1′), O(CH₂)₂(CH₂)_(t)R^(1′), and S(CH₂)₂(CH₂)_(t)R^(1′); alternatively, one R⁴ is a 5-6 membered aromatic heterocycle containing from 1-4 heteroatoms selected from the group consisting of N, O, and S; R^(4a), at each occurrence, is selected from H, ═O, (CH₂)_(r)OR², (CH₂)_(r)—F, (CH₂)_(r)—Br, (CH₂)_(r)—Cl, I, C₁₋₄ alkyl, —CN, NO₂, (CH₂)_(r)NR²R^(2a), (CH₂)_(r)NR²R^(2b), (CH₂)_(r)C(O)R^(2c), NR²C(O)R^(2b), C(O)NR²R^(2a), C(O)NH(CH₂)₂NR²R^(2a), NR²C(O)NR²R^(2a), CH(═NR²)NR²R^(2a), NHC (═NR²)NR²R^(2a), SO₂NR²R^(2a), NR²SO₂NR²R^(2a), NR²SO₂—C₁₋₄ alkyl, C(O)NHSO₂—C₁₋₄ alkyl, NR²SO₂R⁵, S(O)_(p)R⁵, and (CF₂)_(r)CF₃; alternatively, one R^(4a) is a 5-6 membered aromatic heterocycle containing from 1-4 heteroatoms selected from the group consisting of N, O, and S and substituted with 0-1 R⁵; R^(4b), at each occurrence, is selected from H, ═O, (CH₂)_(r)OR³, F, Cl, Br, I, C₁₋₄ alkyl, —CN, NO₂ , (CH₂)_(r)NR³R^(3a), (CH₂)_(r)C(O) R³, (CH₂)_(r)C(O)OR^(3c), NR³C(O)R^(3a), C(O)NR³R^(3a), NR³C(O)NR³R^(3a), CH(═NR³)NR³R^(3a), NH³C(═NR³)NR³R^(3a), SO₂NR³R^(3a), NR³SO₂NR³R^(3a), NR³SO₂—C₁₋₄ alkyl, NR³SO₂CF₃, NR³SO₂-phenyl, S(O)_(p)CF₃, S(O)_(p)—C₁₋₄ alkyl, S(O)_(p)-phenyl, and (CF₂)_(r)CF₃; R⁵, at each occurrence, is selected from CF₃, C₁₋₆ alkyl, phenyl substituted with 0-2 R⁶, and benzyl substituted with 0-2 R⁶; R⁶, at each occurrence, is selected from H, OH, (CH₂)_(r)OR², F, Cl, Br, I, C₁₋₄ alkyl, CN, NO₂, (CH₂)_(r)NR²R^(2a), (CH₂)_(r)C(O)R^(2b), NR²C(O)R^(2b), NR²C(O)NR²R^(2a), CH(═NH)NH₂, NHC(═NH)NH₂, SO₂NR²R^(2a), NR²SO₂NR²R^(2a), and NR²SO₂C₁₋₄ alkyl; R⁷, at each occurrence, is selected from H, OH, C₁₋₆ alkyl, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxy, C₁₋₄ alkoxycarbonyl, (CH₂)_(n)-phenyl, C₆₋₁₀ aryloxy, C₆₋₁₀ aryloxycarbonyl, C₆₋₁₀ arylmethylcarbonyl, C₁₋₄ alkylcarbonyloxy C₁₋₄ alkoxycarbonyl, C₆₋₁₀ arylcarbonyloxy C₁₋₄ alkoxycarbonyl, C₁₋₆ alkylaminocarbonyl, phenylaminocarbonyl, and phenyl-C₁₋₄ alkoxycarbonyl; R⁸, at each occurrence, is selected from H, C₁₋₆ alkyl and (CH₂)_(n)-phenyl; alternatively, R⁷ and R⁸ combine to form a 5 or 6 membered saturated, ring which contains from 0-1 additional heteroatoms selected from the group consisting of N, O, and S; R⁹, at each occurrence, is selected from H, C₁₋₆ alkyl and (CH₂)_(n)-phenyl; n is selected from 0, 1, 2, and 3; m is selected from 0, 1, and 2; p is selected from 0, 1, and 2; r is selected from 0, 1, 2, and 3; s is selected from 0, 1, and 2; and, t is selected from 0 and
 1. 2. A compound according to claim 1, wherein: Z is selected from a bond, CH₂O, OCH₂, CH₂NH, NHCH₂, CH₂C(O), C(O)CH₂, C(O)NH, C(O)NH, CH₂S(O)₂, S(O)₂(CH₂), SO₂NH, and SO₂NH; B is selected from: Y and X-Y; Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R^(4a); phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, 1,3,4-triazole, benzofuran, benzothiofuran, indole, benzimidazole, benzoxazole, benzthiazole, indazole, benzisoxazole, benzisothiazole, and isoindazole; Y may also be selected from the following bicyclic heteroaryl ring systems:

K is selected from O, S, NH, and N.
 3. A compound according to claim 2, wherein Ring M is of formula h:

wherein: D is selected from C(═NR⁷)NR⁸R⁹ and (CR⁸R⁹)NR⁸R⁹; R is selected from H, F, Cl, OR³, CH₂OR³, CH₂NH₂; A is selected from: piperidinyl, piperazinyl, C₅₋₆ carbocyclic residue substituted with 0-2 R⁴, and 5-6 membered heteroaryl containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R⁴; Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R^(4a); phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, and 1,3,4-triazole.
 4. A compound according to claim 3, wherein: E is phenyl; D is selected from C(═NH)NH₂ and CH₂NH₂; R is selected from H, F, Cl, and Br; A is selected from: C₅₋₆ carbocyclic residue substituted with 0-2 R⁴, and 5-6 membered heteroaryl containing from 1-3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R⁴; Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R^(4a); phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, and 1,3,4-triazole; R², at each occurrence, is selected from H, CF₃, C₁₋₆ alkyl, benzyl, C₅₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b); R^(2a), at each occurrence, is selected from H, CF₃, C₁₋₆ alkyl, benzyl, phenethyl, C₅₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b); R^(2b), at each occurrence, is selected from CF₃, C₁₋₄ alkoxy, C₁₋₆ alkyl, benzyl, C₅₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b); R^(2c), at each occurrence, is selected from CF₃, OH, C₁₋₄ alkoxy, C₁₋₆ alkyl, benzyl, C₅₋₆ carbocyclic residue substituted with 0-2 R^(4b), and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R^(4b); alternatively, R² and R^(2a), together with the atom to which they are attached, combine to form a ring selected from imidazolyl, morpholino, piperazinyl, pyridyl, and pyrrolidinyl, substituted with 0-2 R^(4b); R⁴, at each occurrence, is selected from H, ═O, OR², CH₂OR², F, Cl, C₁₋₄ alkyl, NR²R^(2a), CH₂NR²R^(2a), C(O)R^(2c), CH₂C(O)R^(2c), C(O)NR²R^(2a), CH(═NR²)NR²R^(2a), CH(═NS(O)₂R⁵)NR²R^(2a), SO₂NR²R^(2a), NR₂SO₂—C₁₋₄ alkyl, S(O)₂R⁵, and CF₃ provided that if B is H, then R⁴ is other than tetrazole, C(O)-alkoxy, and C(O)NR²R^(2a); R^(4a), at each occurrence, is selected from H, ═O, (CH₂)_(r)OR², F, Cl, C₁₋₄ alkyl, NR²R^(2a), CH₂NR²R^(2a), NR₂R^(2b), CH₂NR²R^(2b), (CH₂)_(r)C(O)R^(2c), NR²C(O)R^(2b), C(O)NR²R^(2a), C(O)NH(CH₂)₂NR²R^(2a), NR²C(O)NR²R^(2a), SO₂NR²R^(2a), S(O)₂R⁵, and CF₃; and, R^(4b), at each occurrence, is selected from H, ═O, (CH₂)_(r)OR³, F, Cl, C₁₋₄ alkyl, NR³R^(3a), CH₂NR³R^(3a), C(O)R³, CH₂C(O)R³, C(O)OR^(3c), C(O)NR³R^(3a), CH(═NR³)NR³R^(3a), SO₂NR³R^(3a), NR³SO₂—C₁₋₄ alkyl, NR³SO₂CF₃, NR³SO₂-phenyl, S(O)₂CF₃, S(O)₂—C₁₋₄ alkyl, S(O)₂-phenyl, and CF₃.
 5. A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
 6. A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound according to claim 2 or a pharmaceutically acceptable salt thereof.
 7. A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound according to claim 3 or a pharmaceutically acceptable salt thereof.
 8. A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound according to claim 4 or a pharmaceutically acceptable salt thereof.
 9. A method for treating a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
 10. A method for treating a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 2 or a pharmaceutically acceptable salt thereof.
 11. A method for treating a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 3 or a pharmaceutically acceptable salt thereof.
 12. A method for treating a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 4 or a pharmaceutically acceptable salt thereof. 